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5% Discount on Legal Highs, Salvia Divinorum and Everything Else From The Coffeesh0p

The Effects of a Novel, Putative 5-HT2a Receptor Agonist on the Creative Process

For my stag night me and a few mates sat in a dark smoke-​​filled room, having ingested a safe amount of legal and uniden­ti­fi­able chem­ical, in pos­ses­sion of a shitty key­board, an awesome syn­thes­izer, an ancient drum machine and some kind of stly­ophone, all fed through a very expensive bass amp. There was also an acoustic guitar lying around.

None of us are very good at music, but this is what we somehow came up with. It was recorded with a phone in the middle of the room.

The Track

It’s not exactly awesome, but I thought I’d stick it up here anyway for you to laugh at, more than anything.

Right, I’m off on hon­ey­moon in 9 hours. I’ll write some­thing else when I get back! Off in half an hour — see you all in two weeks!

Posted in Personal | Tagged 5-ht2a, hallucinogens, Music On Drugs |

We're Married!

In case you were won­dering why I’ve not written any­thing decent for ages, it’s because we’ve been plan­ning our wedding, which finally happened on Sat­urday (May 29th, 2010). I thought I’d put a couple of photos on here today because a few of you seem to actu­ally give a shit, and also then there’s less chance of me for­get­ting any future anniversaries.

If you’ve ever had a decent night out in Birm­ingham, you may recog­nise that as The Custard Factory

During the ceremony

Us in some “arty” doorway

Also, since I’ve still not written a Music On Drugs post, you might like to give some of the music we used in the cere­mony a listen. Links to YouTube open in a new tab/​window.

Before The Ceremony:

Jo Walking Up The Aisle:

Zero 7 — Pop Art Blue

Signing The Register:

Us Walking Out:

Lamb — Gorecki (started at 2:27)

Secular wed­dings are awesome!

(Image credit: Photos of my Wedding)

Posted in Personal | Tagged music, photos, wedding |

Science Joke Winners

Everyone’s a winner who entered last weeks Science Joke Com­pet­i­tion! Not in the sense that everyone wins a prize, but in the sense that maybe, just maybe, we’ve inspired someone, some­where to do some­thing vaguely sci­entific. So who did win a prize? …

The Winner

Potter

There is this farmer who is having prob­lems with his chickens. All of the sudden, they are all getting very sick and he doesn’t know what is wrong with them. After trying all con­ven­tional means, he calls a bio­lo­gist, a chemist, and a phys­i­cist to see if they can figure out what is wrong. So the bio­lo­gist looks at the chickens, exam­ines them a bit, and says he has no clue what could be wrong with them. Then the chemist takes some tests and makes some meas­ure­ments, but he can’t come to any con­clu­sions either. So the phys­i­cist tries. He stands there and looks at the chickens for a long time without touching them or any­thing. Then all of the sudden he starts scrib­bling away in a note­book. Finally, after several grue­some cal­cu­la­tions, he exclaims, ‘I’ve got it! But it only works for spher­ical chickens in a vacuum.

The Runners Up

James

Wanted, dead AND alive: Schrödinger’s Cat

psiphi

Some helium floats into a bar, the bar­tender says “We don’t serve helium in here.”

The helium doesn’t react.

Fant­astic! Remember though, if you’re not from the UK and you want to claim your prize, you’ll have to send us a couple of quid to cover the postage. We’ll sort all that out later. I’ll be in touch soon, prob­ably, although we are getting married in 6 days, so there might be a bit of a delay… :^|

I’ve got to go and write my speech now, so I’ll leave you with this bril­liant sketch from That Mitchell & Webb Look:

Posted in Competitions | Tagged blue lagoon, competition, entheogens, legal highs, mexican dream herb |

Science-Based Quick Competition

Fol­lowing some rather depressing blog com­ments, I reckon it’s about time we had another com­pet­i­tion in the name of science!

What Can You Win?

Blue LagoonBlue Lagoon

The winner will get a super awesome double size bottle of Blue Lagoon, a new liquid herbal high, and a 10g bag of Mexican Dream Herb. The two runners up will just get the Dream Herb.

What Do You Have To Do?

I want to hear the best science joke you’ve got. There’s a few to get you started at the end of this post. Obvi­ously, I don’t expect you to write some new comedy gold, but at least have the decency to tell a joke in your own words and not just lift it from the first google result for “science joeks lol”. Post your entries in the com­ments below this post!

Who Can Enter?

If you’re in the UK, this com­pet­i­tion is for you. If you live any­where else, you can still win the stuff, just as long as you’re willing to PayPal me the postage costs. Usual rules apply, like being over 18, not men­tally unstable or pregnant.

When Will The Winners Be Picked?

Over the next weekend prob­ably. Who knows when exactly… depends when I’ve got 5 minutes. Get off my case already! Jeez.

Posted in Drugs | Tagged blue lagoon, competition, entheogens, legal highs, mexican dream herb |

Synthetic Cannabinoid Discussion

Drugs Discussion


UPDATE: This thread is now closed. Please con­tinue the dis­cus­sion here: Syn­thetic Can­nabinoid Dis­cus­sion II

This post is now the place to comment on the JWH-​​018 Tox­ic­o­logy article.

Not that there are any points, but bonus points for backing up what you say with peer reviewed research. Please keep the dis­cus­sion sci­entific. You can talk about dodgy vendors if you must, espe­cially if there’s a bad batch going round, but please don’t link to them or turn this into a cus­tomer support thread. If you want to talk about indi­vidual smoking mix­tures, please do so Here.

Ok, go:

Posted in Pharmacology | Tagged binding affinities, cannabinoid receptors, JWH-018, jwh-073, synthetic cannabinoids, toxicology |

Smoking Mix Discussion

Drugs Discussion

I’m cre­ating this post so you lot can discuss smoking mix­tures. Feel free to talk about the pros and cons of dif­ferent indi­vidual products, but don’t talk about the vendors them­selves. Com­ments like ‘This shiz I got from buy​drugslmao​.com is suh­weeet” will be deleted.

Ok, go:

Posted in Drugs | Tagged discussion, smoking mixtures |

How To Make A Bomb

No, this post won’t be a detailed guide to clandes­tine hexa­methylene triper­oxide diamine man­u­fac­ture, sorry! Instead of ter­rorism, today’s post will focus on a great harm reduc­tion tech­nique called bombing (or para­chuting for us in the far-​​less-​​extreme UK).

The Problem:

You have a bag of a drugs. That bag of drugs can be snorted, or it can be eaten.  Unfor­tu­nately, your nose wasn’t meant for hoovering up monster lines of chem­ical. Apart from the phys­ical irrit­a­tion to your del­icate mucous mem­branes, vaso­con­strictive drugs like cocaine or mephed­rone will restrict blood­flow in the vessels lining your nose, which could lead to ischaemia, or the damage of tissue as a result of poor blood per­fu­sion. If that wasn’t bad enough, pretty soon, your nose might start pouring with snot or just feel bunged up when the drug wears off, as the blood vessels open back up to com­pensate — your nose isn’t blocked with snot or drugs neces­sarily, but by these vessels filling up with blood, which closes off your nos­trils, making it harder to breath.

Suppose at this point, you still have most of your massive bag of drugs left — what do you do? Perhaps the most instinctive thing to do is reach for some­thing to unblock your nose, such as a decon­gestant spray or some “Vaporub” type stuff, so you can con­tinue your hedon­istic nasally-​​orientated pleasure-​​binge. It might sur­prise you to learn that this won’t help out your stinging nos­trils as much as you think. These kind of products work by con­stricting those same blood vessels that were con­stricted earlier, adding to the ischaemia. If that wasn’t enough, con­tinued use of these kinds of products could give you rebound con­ges­tion — as soon as you stop using them, your vessels open back up to com­pensate and before you know it, you’re adding an extra “b” to every word you say ended with a bil­a­bial phone.

That’s just the phys­ical side of things. Snorting drugs does get them into your blood faster, sure, but this also makes whatever you’re snorting more addictive. With our old friend mephed­rone, snorting cer­tainly can be fun, but it’s much easier to have “just one more line” another ten times in the same session than if you ate it.

The Solution:

If your bag of drugs also works well when eaten, eat that shit! Obvi­ously no one wants to be chucking fist­fulls of dis­gusting powder into their mouths, which is where our friend the bomb comes into play.

Step 1: Get Your Shit Together


You will need:

  • Rizlas (or whatever brand of rolling paper is most pre­valent where you’re from)
  • A bag of drugs
  • Some­thing to transfer the drugs from the bag to the papers

Step 2: Take A Single Paper

Step 3: Tear Off The Excess


You don’t need much, prob­ably about an inch or so.

Step 4: Transfer Your Drugs To The Paper


Safety first! If your drug of choice requires only a few mili­grams, or you’re gen­er­ally unsure how to eyeball a dose, weigh it out first, then transfer it to the paper.

Step 5: Pick Up The Paper


Get the paper to fold nat­ur­ally, as though you’re about to roll the world’s tiniest joint packed with chemicals.

Step 6: Pinch The Paper


Pinch one end of the paper, so you can hold it at an angle and tap the powder into the pinched end.

Step 7: Pinch T'Other Side


Repeat step 6 with the other side, so the powder takes up as little room as possible.

Step 8: Pinch Both Sides


This step should get your little pile of drugs in the centre of your paper. Don’t be afraid to com­press it a little so it stays in place. The last thing you want is stray drugs working them­selves free and onto your taste buds.

Step 9: Begin To Form A Tail


No, don’t actu­ally grow a tail. Just pull together the pinched ends of the paper, so the drugs are at one end and the free bits are together at the other.

Step 10: Form A Tail


Pinch all the excess paper into one clump between your thumb and finger.

Step 11: Complete The Tail


Now roll the tail betwixt your thumb and finger to tighten it. Feel free to lick your fingers first to help it seal, but not too much, or you’ll be left with a wet powdery mess.

Step 12: Marvel At Your Creation


Now it’s time to stick it to the infidel! Erm, I mean, take your drugs safely.

Nice work!

(Pic­tures provided by methuselah969)

Posted in Teks | Tagged bombing, harm reduction, parachuting |

Mephedrone Banned On Friday 16th April

Fol­lowing the ACMD’s report on the cath­inone deriv­at­ives (Part I & Part II), here is the latest amend­ment to the Misuse of Drugs Act to control them:

Dan­gerous Drugs, England And Wales
Dan­gerous Drugs, Scot­land
The Misuse of Drugs (Amend­ment) (England, Wales and Scot­land) Reg­u­la­tions 2010

Made
31st March 2010

Laid before Par­lia­ment
1st April 2010

Coming into force
16th April 2010

The Sec­retary of State makes the fol­lowing Reg­u­la­tions in exer­cise of the powers con­ferred by sec­tions 7, 10, 22 and 31 of the Misuse of Drugs Act 1971(1).

In accord­ance with section 31(3) of that Act the Sec­retary of State has con­sulted with the Advisory Council on the Misuse of Drugs.
Cita­tion, com­mence­ment, inter­pret­a­tion and extent

1. — (1) These Reg­u­la­tions may be cited as the Misuse of Drugs (Amend­ment) (England, Wales and Scot­land) Reg­u­la­tions 2010 and shall come into force on 16th April 2010.

(2) In these Reg­u­la­tions “the 2001 Reg­u­la­tions” means the Misuse of Drugs Reg­u­la­tions 2001(2).

(3) These Reg­u­la­tions extend to England, Wales and Scot­land.
Amend­ment to the 2001 Regulations

2. The 2001 Reg­u­la­tions shall be amended as follows.

3. In Schedule 1 (which spe­cifies con­trolled drugs subject to the require­ments of reg­u­la­tions 14, 15, 16, 18, 19, 20, 23, 26 and 27)—

(a) in para­graph 1(a), after “meth­cath­inone”, insert—

“4 – methylmethcathinone”;

(b) after para­graph 1(l), insert—

“(m) Any com­pound (not being bupro­pion, diethyl­pro­pion, pyro­va­lerone or a com­pound for the time being spe­cified in sub – para­graph (a) above) struc­tur­ally derived from 2 – amino – 1 – phenyl – 1 – pro­panone by modi­fic­a­tion in any of the fol­lowing ways, that is to say—

(i) by sub­sti­tu­tion in the phenyl ring to any extent with alkyl, alkoxy, alkyle­ne­dioxy, haloalkyl or halide sub­stitu­ents, whether or not further sub­sti­tuted in the phenyl ring by one or more other uni­valent substituents;

(ii) by sub­sti­tu­tion at the 3 – pos­i­tion with an alkyl substituent;

(iii) by sub­sti­tu­tion at the nitrogen atom with alkyl or dialkyl groups, or by inclu­sion of the nitrogen atom in a cyclic structure.”.

David Hanson
Min­ister of State
Home Office
31st March 2010

Let’s take a look at this and try and make some sense of it shall we?

(a) in para­graph 1(a), after “meth­cath­inone”, insert—

“4 – methylmethcathinone”;

First off, mephed­rone (4-​​methylmethcathinone) is expli­citly men­tioned to appear after meth­cath­inone, which is already class B. I suppose we knew that much was going to happen already, so onto the more com­plic­ated stuff…

(b) after para­graph 1(l), insert—

“(m) Any com­pound (not being bupro­pion, diethyl­pro­pion, pyro­va­lerone or a com­pound for the time being spe­cified in sub – para­graph (a) above) struc­tur­ally derived from 2 – amino – 1 – phenyl – 1 – pro­panone by modi­fic­a­tion in any of the fol­lowing ways, that is to say—

This means that any cath­inone deriv­ative described by any of the fol­lowing para­graphs will also become class B. Like the can­nabin­oids banned last December, this ban doesn’t list a tonne of indi­vidual sub­stances, but instead covers a wide range of actual and the­or­et­ical sub­stances by detailing pos­sible alter­a­tions to the ori­ginal cath­inone struc­ture. Here they are:

(i) by sub­sti­tu­tion in the phenyl ring to any extent with alkyl, alkoxy, alkyle­ne­dioxy, haloalkyl or halide sub­stitu­ents, whether or not further sub­sti­tuted in the phenyl ring by one or more other uni­valent substituents;

This first part covers modi­fic­a­tions of the phenyl ring, or “round bit” of the cath­inone struc­ture (R4). Unfor­tu­nately, this covers a massive range of com­pounds, including Mephed­rone (alkyl), Methed­rone (alkoxy), Methylone, Ethylone, Butylone & MDPV (all alkyle­ne­dioxy) and flephed­rone (halide; also includes the 3-​​F isomer) .

(ii) by sub­sti­tu­tion at the 3 – pos­i­tion with an alkyl substituent;

This covers the addi­tion of a carbon side chain of any length on the carbon atom just before the nitrogen atom (usually referred to as the alpha carbon).  All the com­pounds listed in Annex A,  Appendix 1 of the ACMD’s report include a chain of at least one carbon long (alpha methyl­a­tion), but by not spe­cifying the length of this “alkyl sub­sti­tute”, this also covers  existing com­pounds with longer alpha side chains such as pentylone and MDPV as well as any poten­tially inter­esting the­or­et­ical compounds.

(iii) by sub­sti­tu­tion at the nitrogen atom with alkyl or dialkyl groups, or by inclu­sion of the nitrogen atom in a cyclic structure.”

The final nitrogen atom present in cath­inone has two avail­able places to add stuff. One or both of these could be a carbon chain (alkyl or dialkyl), or a single carbon chain could form a ring by starting and ending at this nitrogen atom (the “cyclic struc­ture”), which is what this part covers. Examples include eth­cath­inone (alkyl — a single carbon chain), n,n-dimethylcathinone (dialkyl — two carbon chains) and MDPV (includes the cyclic pyrrolid­inyl structure).

I know that’s still quite tech­nical, but hope­fully what I’ve written is a little clearer than the ori­ginal text. Feel free to ask ques­tions in the com­ments though!

The gist is, all the popular cath­inone deriv­at­ives men­tioned by name above will become class B on Friday 16th, as well as a great deal of the more eso­teric ones. One com­pound not included in this ban is naphyrone, cur­rently mar­keted as Energy-​​1 or NRG-​​1. Unfor­tu­nately, I hear it’s rather shit and also not par­tic­u­larly safe, but the ACMD are already looking into banning that for next time. That’s pretty much it for cath­inones in the UK then. I feel like we should all go out and get com­mem­or­ative T-​​shirts or some­thing… :(

On a more serious note, for those pre­vi­ously law abiding cit­izens who have developed a psy­cho­lo­gical addic­tion to mephed­rone, you have two choices: con­tinue buying lower quality stuff at an inflated price from a regular drug dealer or find some help. Luckily, Drug​-Forum​.com has a great Recovery and Addic­tion section that you should def­in­itely check out.  You’re also welcome to post your stories and pro­gress in the com­ments under this post.

Posted in Legislation | Tagged ACMD, addiction, butylone, cathinone, classification, dimethylcathinone, energy-1, ephedrone, mdpv, mephedrone, methylone, naphyrone, nrg-1, pentylone |

Shaun The Sheep

My last two posts have been a bit hard going, so here’s a little some­thing to lighten the mood:

Ok, so now you’re addicted Shaun The Sheep instead of mephedrone.

Although Shaun The Sheep provides me with a cheap, 10 minute euphoria, at least it’s off the ACMD’s radar… for now! Just make sure you only tell your respons­ible friends about this so our nation’s kids don’t start getting hold of it. That said, you may want to start stock­piling the epis­odes on DVD before the inevitable.

Also, in case you’re won­dering what a couple in their 20’s are doing watching kid’s telly, FUCK YOU, that’s what!

Posted in Drugs | Tagged ACMD, mephedrone, shaun the sheep, tv |

The ACMD’s Mephedrone Report Part II

This post con­tains the important annexes from the ACMD’s report on mephed­rone and related cath­inones. You can read the main body of the report here: The ACMD’s Mephed­rone Report Part I. The ori­ginal pdf is linked to at the end of this post.

I’ll prob­ably write a few com­ments about the entire report in my next post, whenever that may be. Anyhoo…

Annex A. Recommendation For The Generic Control Of The Cathinone Derivatives

Scope of a generic definition

The ACMD here set out recom­mend­a­tions on the range of com­pounds that should be included in a generic defin­i­tion for the control of cath­inone deriv­at­ives under the Misuse of Drugs Act 1971.

It was pro­posed that the scope of com­pounds covered by generic control should be much wider than the 6 ring sub­sti­tuted com­pounds listed in Table 1 (annex A) and wider than the 10 com­pounds reported to the EMCDDA since 2006.

The scope should include all cath­inone deriv­at­ives that have been found in seizures and col­lected samples together with com­pounds that have not been encountered but have misuse poten­tial. This includes cath­inone deriv­at­ives with and without ring sub­stitu­ents and with side chains longer than those usually encountered in the phen­ethyl­amine drugs.

The scope should also include any sub­stances known or believed to be pro-​​drugs, i.e. sub­stances that are meta­bol­ised to a known active sub­stance (for example GBL is con­verted in the body to GHB).

The generic defin­i­tion should not include those sub­stances already con­trolled under the Misuse of Drugs Act, i.e. diethyl­pro­pion (Class C), cath­inone (Class C), meth­cath­inone (Class B) and pyro­va­lerone (Class C). Finally the defin­i­tion should not include any sub­stances, e.g. bupro­pion, that are ingredi­ents of legit­imate phar­ma­ceut­ical products or that have other legit­imate uses.

The struc­ture of cath­inone deriv­at­ives is rep­res­ented by the gen­er­al­ised struc­ture below:

Figure 1: Gen­er­al­ised struc­ture of cath­inone deriv­at­ives
where,

R1= single alkyl group [but not H]
R2= H or alkyl
R3= H or alkyl or
[NR2R3] = pyrrolidino or phthalimido or other ring structure
R4= H (no sub­stitu­ents) or
= one or more of alkyl, alkoxy, alkyle­ne­dioxy and halide whether or
not further sub­sti­tuted with an other uni­valent substituent

The phthalimido group has so far only been encountered in the com­pound a-​​phthalimidopropiophenone. This sub­stance has been found in a capsule in com­bin­a­tion with 2-​​fluoromethcathinone and in cap­sules con­taining a mixture with 4-​​methylmethcathinone, N-​​ethylcathinone, and caffeine.

The reason for adding a-​​phthalimidopropiophenone is not clear. It may have been added delib­er­ately, perhaps as a pro-​​drug for cath­inone, but there is no inform­a­tion about its phar­ma­co­logy or meta­bolism. This sub­stance is also an inter­me­diate in the syn­thesis of cath­inone and N-​​alkyl deriv­at­ives of cath­inone. It could there­fore be present unin­ten­tion­ally as a residue of an inter­me­diate, the product of a failed chem­ical syn­thesis, or even the miss-​​labelling of an intermediate.

In addi­tion to com­pounds with the gen­er­al­ised struc­ture in (Figure 1, Annex A) the phenyl ring can be replaced with a naph­thyl ring (e.g. Figure 2, Annex A) or with a thiophene ring. The naph­thyl ana­logue of pyro­va­lerone (Figure 2, Annex A) is avail­able on the Internet and is being retailed as “NRG-​​1”. These com­pounds cannot easily be included in a generic defin­i­tion for the cath­inone deriv­at­ives having the gen­er­al­ised struc­ture in Figure 1, Annex A, but they could be con­trolled as named sub­stances or by one or more sep­arate generic defin­i­tions. The ACMD intend to review these sub­stances and provide further advice at a later date.

Figure 2: Naph­thyl ana­logue of pyrovalerone

The sys­tem­atic chem­ical name for the struc­ture in Figure 2, Annex A is 1-(2-naphthyl)-2-(1-pyrrolidinyl)-1-pentanone and altern­ative names include naph­thylpyro­va­lerone, naphyrone and O-​​2482.

Appendix I, of this Annex includes all the cath­inone deriv­at­ives, with the general struc­ture in Figure 1, Annex A, that have been encountered in seizures and col­lected samples, sub­stances that are already con­trolled, ingredi­ents of known phar­ma­ceut­ical products, sub­stances avail­able via the Internet and sub­stances that are listed in Wiki­pedia. However, the market for cath­inone deriv­at­ives is still evolving and new sub­stances will con­tinue to appear.

Many cath­inone deriv­at­ives are men­tioned in patents for phar­ma­ceut­ical applic­a­tions but the only known non-​​controlled cath­inone deriv­ative with a mar­keting author­isa­tion appears to be bupro­pion, an ingredient of ®Zyban.

Some cath­inone deriv­at­ives are men­tioned in patents for non-​​pharmaceutical applications.

A structure-​​based search of the 12th Edition of the Merck Index (1996), carried out pre­vi­ously by Dr Les King, found no con­ten­tious compounds.

Inter­est­ingly, a recent patent (WO PCT 2010006196) relating to water puri­fic­a­tion mem­branes men­tions the com­pound in Figure 3 below, which is closely related to methylone (bk-​​MDMA). This com­pound would be included within a generic defin­i­tion since the term methyl­e­ne­dioxy can have two mean­ings. However, com­pounds ana­logous to those in Figure 3, Annex A are unlikely to have any com­mer­cial uses.

Figure 3: 3,4-methylenedioxy-N-methyl-ß-keto-amphetamine

Structure Activity Relationships

Cath­inone deriv­at­ives have a range of effects (e.g. stim­u­lant, empath­ogen and antidepressant).

The cath­inone deriv­at­ives without ring sub­stitu­ents (e.g. diethyl­pro­pion, meth­cath­inone, buphed­rone, N,N-dimethylcathinone) are mostly stimulants.

Most of the cath­inone deriv­at­ives encountered as legal highs are ring sub­sti­tuted com­pounds with a sec­ondary amino group (R2 = methyl or ethyl and R3 = hydrogen) or with a cyclic amino group (NR2R3 = pyrrolidino group or phthalimido group). These sub­stances are primarily stim­u­lants, with varying degrees of empath­o­genic effects (i.e. similar in effects to MDMA). Ring sub­stitu­ents (R4) have included alkyl, alkoxy, methyl­e­ne­dioxy and halide.

The side chain sub­stituent (R1) has mostly been a single alkyl group. However there are examples with allyl (an alkenyl) and pro­pargyl (an alkynyl) groups and also examples with a second alkyl group attached to the same carbon atom as R1, but these com­pounds are not within the pro­posed scope.

No haloalkyl sub­stitu­ents (e.g. tri­fluoro­methyl –CF3 as found in piperazine deriv­at­ives) in the ring (R4) or on the side chain (R1) have been encountered or reported in the lit­er­ature. However, replace­ment of the ring methyl group, as in mephred­rone, with a tri­fluoro­methyl group is likely to produce sub­stances with similar activ­ities. It is recom­mended there­fore that haloalkyl sub­stitu­ents be included in the generic defin­i­tion for ring substituents.

Cath­inone deriv­at­ives with a primary amino group (i.e. no N-​​alkyl sub­stitu­ents) are rarely encountered, pos­sibly because of their instability. There are only two known examples, bk-​​MDA (known to sub­sti­tute for MDMA in rats) and cath­inone (a stimulant).

The NR2R3 amino groups reported in the sci­entific lit­er­ature have included alkylamino (R2 = alkyl, R3 = H), dial­kylamino (R2 =alkyl, R3 = alkyl), the cyclic pyrrolidino group and a large number of other cyclic amines. However, for the pyro­va­lerone ana­logues an increase in size of the nitrogen con­taining ring from a five-​​membered pyrrolidine ring to a six-​​membered piperidine ring res­ulted in a sub­stan­tial loss in binding potency. There are also examples of N-​​allyl, N-​​propargyl and N-​​cycloalkyl substituents.

The anti-​​depressant drug bupro­pion has a tertiary-​​butyl group on the nitrogen atom and several other sub­stances invest­ig­ated for their poten­tial as smoking ces­sa­tion drugs also have a bulky alkyl group on the nitrogen atom, e.g. tertiary-​​butyl, iso-​​propyl or cyc­loalkyl, or the alkyl amino group is replaced by a cyclic piperidino group (a cyclic amino group with 6 membered ring).

Salts, stereoisomers, esters and ethers

Cath­inone deriv­at­ives with the gen­er­al­ised struc­ture in Figure 1, Annex A, all have an asym­metric a-​​carbon atom giving rise to R and S stereoisomers.

With the excep­tion of the phthalimido deriv­at­ives, all cath­inone deriv­at­ives have a basic nitrogen atom and can there­fore form salts.

There is no defin­i­tion of esters and ethers in the Misuse of Drugs Act 1971, but from a chem­ical per­spective esters usually only applies to deriv­at­ives of acids with a hydroxyl group, and deriv­at­ives of alco­hols and phenols. Like­wise ethers usually only applies to deriv­at­ives of alco­hols and phenols. On this basis the cath­inone deriv­at­ives would not form esters or ethers.

However, keto com­pounds, R1R2C=O, can form ketals, R1R2C(OR’)2, which argu­ably might be described as a special form of an ether. Ketals of cath­inone deriv­at­ives have been dis­cussed on drug forums in the context of a pro-​​drug and are men­tioned in the sci­entific lit­er­ature, usually as a means of pro­tecting the keto group during chem­ical syntheses.

Generic definition for the control of cathinone derivatives

The ACMD have con­sidered a number of options for the control of cath­inone deriv­at­ives, including listing of named sub­stances, several generic defin­i­tions and com­bin­a­tions of these approaches.

Taking into account the ACMD’s con­sid­er­a­tion of the scope, together with struc­ture activity rela­tion­ships and pre­val­ence of known cath­inone deriv­at­ives, the fol­lowing generic defin­i­tion is recommended:

Any com­pound (not being bupro­pion or a sub­stance for the time being spe­cified in para­graph 2.2) struc­tur­ally derived from 2-​​amino-​​1-​​phenyl-​​1-​​propanone by modi­fic­a­tion in any of the fol­lowing ways, that is to say,

  1. by sub­sti­tu­tion in the phenyl ring to any extent with alkyl, alkoxy, alkyle­ne­dioxy, haloalkyl or halide sub­stitu­ents, whether or not further sub­sti­tuted in the phenyl ring by one or more other uni­valent substituents;
  2. by sub­sti­tu­tion at the 3-​​position with an alkyl substituent;
  3. by sub­sti­tu­tion at the nitrogen atom with alkyl or dialkyl groups, or by inclu­sion of the nitrogen atom in a cyclic structure.

Notes

  • the parent com­pound is cathinone
  • “any” is taken to mean one or more

Com­ments

This is a defin­i­tion that includes all per­muta­tions for the three sub­sti­tu­tion areas, i.e. in the ring (R4), in the side chain (R1) and on the nitrogen (NR2R3).

  • All the cath­inone deriv­at­ives would be in the same Class which would result in some anom­alies for com­pounds already controlled.
  • Includes all the com­pounds in Appendix 1.
  • Includes primary amines without ring sub­stitu­ents (no known examples, except cath­inone which is not included within the scope of this definition).
  • Includes ring sub­sti­tuted primary amines (bk-​​MDA is the only example).
  • The term “cyclic struc­ture” has a very wide scope (e.g. all ring sizes, all het­ero­cyclic nitrogen com­pounds and struc­tures with ring substituents).

Appendix 1

Cath­inone
(Class C)
beta-​​keto-​​amphetamine

Note: only encountered in Khat although it has been encountered as the pro-​​drug, a-​​phthalimidopropiophenone (see below)

R1 = Me
R2 = H
R3 = H
R4 = H
Cathinone
a-​​phthalimidopropiophenone

Note: found in products from the Internet

R1 = Me
NR2R3 = phthalimide
R4 = H
a-phthalimidopropiophenone
Meth­cath­inone
(Class B)
Ephed­rone
a-​​methylaminopropiophenone
R1 = Me
R2 = Me
R3 = H
R4 = H
Methcathinone
N,N-Dimethylcathinone
Metam­fe­pra­mone
Dimethylpropion

Note: encountered in seizures

R1 = Me
R2 = Me
R3 = Me
R4 = H
N,N-Dimethylcathinone
Eth­cath­inone
Ethyl­pro­pion
N-​​ethylcathinone
2-​​ethylamino-​​propiophenone
Sub Coca II

Note: encountered in seizures

R1 = Me
R2 = Et
R3 = H
R4 = H
Ethcathinone
Diethyl­pro­pion
(Class C)
Diethyl­cath­inone
Amfepramone
R1 = Me
R2 = Et
R3 = Et
R4 = H
Diethylpropion
a-​​Pyrrolidinopropiophenone
a-​​PPP

Note: encountered in Germany

R1 = Me
NR2R3 = Pyrrolid­inyl
R4 = H
a-Pyrrolidinopropiophenone
Buphed­rone
2-​​methylamino-​​1-​​phenylbutan-​​1-​​one

Note: no seizures reported to EMCDDA but is avail­able via the Internet and user reports are on drug forums.

R1 = Et
R2 = Me
R3 = H
R4 = H
Buphedrone
a-​​Pyrrolidinobutiophenone
a-​​PBP

Note: no seizure or user reports but listed on Wiki­pedia and in a patent

R1 = Et
NR2R3 = Pyrrolid­inyl
R4 = H
a-Pyrrolidinobutiophenone
a-​​Pyrrolidinovalerophenone
a-​​PVP
a-​​Pyrrolidinopentiophenone

Note: No seizures reported to EMCDDA, but meta­bolism study by Germany, as a result of 2 seizures, in Germany and Netherlands.

R1 = n-​​Pr
NR2R3 = Pyrrolid­inyl
R4 = H
a-Pyrrolidinovalerophenone
Mephed­rone
4-​​Methylmethcathinone
4-​​MMC
Sub Coca I

Note: most fre­quently encountered cath­inone derivative

R1 = Me
R2 = Me
R3 = H
R4 = 4-​​Me
Mephedrone
4’-methyl-a-pyrrolidinopropiophenone
MPPP

Note: seizure report from Germany

R1 = Me
NR2R3 = Pyrrolid­inyl
R4 = 4-​​Me
4’-methyl-a-pyrrolidinopropiophenone
4’-methyl-a-pyrrolidinobutiophenone
MPBP

Note: seizure report from Germany

R1 = Et
NR2R3 = Pyrrolid­inyl
R4 = 4-​​Me
4’-methyl-a-pyrrolidinobutiophenone
Pyro­va­lerone
(Class C)
R1 = n-​​Pr
NR2R3 = Pyrrolid­inyl
R4 = Me
Pyrovalerone
4’-methyl-a-pyrrolidinohexiophenone
MPHP

Note: seizure report from Germany

R1 = n-​​Bu
NR2R3 = Pyrrolid­inyl
R4 = Me
4’-methyl-a-pyrrolidinohexiophenone
Methed­rone
4-​​methoxymethcathinone
PMMC
bk-​​PMMA

Note: encountered in seizures

R1 = Me
R2 = Me
R3 = H
R4 = 4-​​MeO
Methedrone
4’-Methoxy-a-pyrrolidinopropiophenone
MOPPP

Note: seizure report from Germany

R1 = Me
NR2R3 = Pyrrolid­inyl
R4 = 4-​​MeO
Bupro­pion
(Zyban – medi­cinal product in UK)

Note: To be excluded from control. No reports of abuse)

R1 = Me
R2 = t-​​Bu
R3 = H
R4 = 3-​​Cl
Bupropion
Flephed­rone
4-​​Fluoromethcathinone
4FMC

Note: encountered in seizures. The 3-​​fluoro and 2-​​fluoro isomers have also been found in products from the Internet.

R1 = Me
R2 = Me
R3 = H
R4 = 4-​​F
(also 2-​​F and 3-​​F)
Flephedrone
Methylone
3,4-Methylenedioxymethcathinone
bk-​​MDMA

Note: encountered in seizures

R1 = Me
R2 = Me
R3 = H
R4 = 3,4-methylenedioxy
Methylone
Ethylone
3,4-methylenedioxyethcathinine
bk-​​MDEA

Note: encountered in seizures

R1 = Me
R2 = Et
R3 = H
R4 = 3,4-methylenedioxy
Ethylone
3’,4’-methylenedioxy-a-pyrrolidinopropiophenone
MDPPP

Note: seizure reports from Germany and Denmark

R1 = Me
NR2R3 = Pyrrolid­inyl
R4 = 3,4-methylenedioxy
3’,4’-methylenedioxy-a-pyrrolidinopropiophenone
Butylone
ß-keto-N-methyl-3,4-benzodioxyolylbutanamine
bk-​​MDBD

Note: seizure reports from 7 countries

R1 = Et
R2 = Me
R3 = H
R4 = 3,4-methylenedioxy
Butylone
3’,4’-Methylenedioxy-a-pyrrolidinobutiophenone

Note: no seizure reports, but men­tioned in Wiki­pedia and in patent

R1 = Et
NR2R3 = Pyrrolid­inyl
R4 = 3,4-methylenedioxy
3’,4’-Methylenedioxy-a-pyrrolidinobutiophenone
Pentylone
ß-​​Keto-​​methylbenzodioxolylpentanamine
bk-​​Methyl-​​K
bk-​​MBDP

Note: no seizure reports, but men­tioned in Wiki­pedia and in patent.

R1 = n-​​Pr
R2 = Me
R3 = H
R4 = 3,4-methylenedioxy
Pentylone
Methyl­e­ne­di­oxypyro­va­lerone
MDPV

Note: encountered in seizures

R1 = n-​​Pr
NR2R3 = Pyrrolid­inyl
R4 = 3,4-methylenedioxy
Methylenedioxypyrovalerone

Annex B & C

…Aren’t really worth including here. They contain a list of ACMD members and a list of organ­isa­tions and indi­viduals who sub­mitted evid­ence included in the report. Go and read it in the ori­ginal pdf if you want to. Go on! Go and bloody read it!

Annex D. Letter From The Advisory Council On The Misuse Of Drugs To The Home Secretary

22nd December 2009

Dear Home Secretary,

Re: ACMD con­sid­er­a­tion of mephed­rone (and related cathinones)

The ACMD wrote to you in March to explain that it would be pleased to accede to the Government’s pri­or­ities that your pre­de­cessor set out in her letter of 13 March 2009. Con­cerning the issue of ‘legal highs’ the ACMD has provided advice on the syn­thetic can­nabinoid receptor agon­ists (Spice), 1-​​benzylpiperazine, GBL and 1,4-BD all of which we note will be con­trolled in the legis­la­tion on the 23rd December. In the ACMD’s letter of 30 September 2009 it was explained that we would next provide you with advice on the cathinones.

Despite the dif­fi­culties of the last 2 months the ACMD is com­mitted to providing you with advice on the cath­inones. Although atten­tion has focused on mephed­rone, five other syn­thetic psy­cho­active cath­inone deriv­at­ives are also widely avail­able. The ACMD explained in a pre­vious letter to you that it has con­cerns about the apparent pre­val­ence and poten­tial harms of these com­pounds. Much has been made of these com­pounds in the media over recent weeks; we find it of concern that this may have had the con­sequence of bringing such drugs to the atten­tion of a wider demo­graphic sooner than may have been the case.

The ACMD under­stand that mephed­rone, amongst other cath­inones, is being mar­keted as a variety of appar­ently ‘benign’ products e.g. bath salts or plant food. Whilst the poten­tial harms of these drugs are not yet fully known, it is apparent that the selling of such unreg­u­lated pre­par­a­tions in a form that they are clearly unin­tended for could have serious public health implications.

The ACMD is mindful that, after recent events, our stat­utory mem­ber­ship require­ments need to be ful­filled before providing formal advice, according to the require­ments of the Misuse of Drugs Act 1971. However, the ACMD would like to assure you that it will seek to provide you with such advice at the earliest pos­sible oppor­tunity on this important issue.

I would be willing to discuss the issue of the cath­inones and, more broadly, new psy­cho­active sub­stances (‘legal highs’) and the timing of advice with you.

Yours sin­cerely,

Pro­fessor Les Iversen
(on behalf of the ACMD)

***

The ori­ginal (bor­ingly formatted) report can be found here: ACMD-cathinones-report.pdf

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