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Ivory Wave Destined For Class B

By John Clarke

Or at least that’s how the media will inev­it­ably sim­plify it for all you plebs out there, who couldn’t pos­sibly need to know, let alone under­stand, the exact wording of the law. On the 13th of September, everyone’s favourite council of advisors, the Advisory Council on the Misuse of Drugs (ACMD) released their report on Desoxypi­pra­drol (2-​​DPMP), including advice for another broad ana­logue ban similar to the bans of the cath­inones & can­nabin­oids in the not too distant past.

Here’s the first part of the report, formatted and presented in lovely HTML (Annex 2 will be posted up soon.):

Consideration of Desoxypipradrol (2-DPMP) and related pipradrol compounds

Letter To The Home Secretary From The ACMD

13th September 2011Dear Home Secretary,

I write further to my cor­res­pond­ence of 29 October 2010 in rela­tion to the com­pound desoxypi­pra­drol (2-​​diphenylmethyl-​​piperidine, 2-​​DPMP). In its advice the Advisory Council on the Misuse of Drugs (ACMD) recom­mended that desoxypi­pra­drol, iden­ti­fied in samples of a product known as „Ivory Wave?, should be subject to an imme­diate ban under the Open General Import Licence. This advice was accepted by the Gov­ern­ment and a ban was imple­mented on 4 November 2011.

The ACMD has con­sidered the avail­able evid­ence and can now provide you with sub­stantive con­sid­er­a­tion of the com­pound desoxypi­pra­drol and its related com­pounds. A short report is annexed to this letter.

The National Poisons Inform­a­tion Service in Edin­burgh high­lighted that a number of indi­viduals had presented to the Royal Edin­burgh Infirmary in the summer of 2010 fol­lowing use of desoxypi­pra­drol with symp­toms that were similar to amphet­amine tox­icity, but with pre­dom­inant neuro­psy­chi­atric fea­tures including:

  • Hal­lu­cin­a­tions
  • Para­noia
  • Severe Agit­a­tion

In some cases these effects per­sisted for several days after ingestion.

In the attached report the ACMD has con­sidered the avail­able evid­ence from forensic pro­viders, the National Pro­gramme on Sub­stance Abuse Deaths, Clin­ical Tox­ic­o­logy Ser­vices, sci­entific research and Gov­ern­ment Depart­ments on the harms and sales of desoxypipradrol.

The ACMD advises that the harms of desoxypi­pra­drol are com­men­surate with other Class B drugs and recom­mend that it is con­trolled under the Misuse of Drugs Act 1971 as a Class B sub­stance and in Schedule 1 of the Misuse of Drugs Reg­u­la­tions 2001 (as amended). In addi­tion, the ACMD recom­mends that the struc­tur­ally related com­pounds diphen­yl­pro­linol (diphenyl-​​2– pyrrolidinyl-​​methanol, D2PM) and its desoxy form 2-​​diphenylmethylpyrrolidine are con­trolled under the Misuse of Drugs Act 1971 as Class B sub­stances and sched­uled under the Misuse of Drugs Reg­u­la­tions 2001. The pro­posed generic defin­i­tion will ensure that desoxypi­pra­drol and all its related com­pounds, e.g. diphen­yl­pro­linol and diphen­yl­methyl­pyrrolidine, are fully cap­tured (see Annex 1 & 2). The ACMD under­stands that desoxypi­pra­drol and its related com­pounds do not have any medi­cinal uses; however, the ACMD has not form­ally con­sulted with the industry.

The ACMD believes that there would be no con­flicting issues with placing the generic defin­i­tion in the Act as the three main drugs, desoxypi­pra­drol, diphen­yl­pro­linol (D2PM) and 2-​​diphenylmethylpyrrolidine can all be ana­lyt­ic­ally dis­tin­guished from one another and from other drugs in Schedule 2 Part II.

The pos­i­tional isomers of pipra­drol (diphenyl-​​2-​​piperidinemethanol), i.e. the diphenyl-​​3-​​piperidinemethanol and diphenyl-​​4– piperid­ine­meth­anol isomers would be Class B and in the absence of ref­er­ence stand­ards may not be readily dis­tin­guished from pipra­drol (Class C) using routine methods of ana­lysis (medi­cinal products con­taining pipra­drol are no longer widely used and are not, as far as the ACMD are aware, avail­able in the UK). Whilst, it should be pos­sible to dis­tin­guish between pipra­drol isomers using tech­niques such as NMR, in the long term it would be support forensic ana­lysis to have ref­er­ence stand­ards of all the pipra­drol pos­i­tional isomers.

The ACMD recom­mends that the Home Office con­siders com­mis­sioning the pro­duc­tion of stand­ards through the Forensic Early Warning System.

Yours sin­cerely,

Pro­fessor Les Iversen FRS

(cc: Anne Milton – Par­lia­mentary Under Sec­retary of State, Depart­ment of Health)

1. Background

In October 2010 the ACMD recom­mended to the Gov­ern­ment that, 2– diphenylmethyl-​​piperidine (2-​​DPMP, here referred to as desoxypi­pra­drol), which was being mar­keted at that time as “Ivory Wave”, should be subject to an imme­diate ban under the Open General Import Licence (OGIL). This advice was accepted by the Gov­ern­ment and a ban was imple­mented on 4 November 2011

Pub­lished data on the effects of 2-​​DPMP are limited, although research on deriv­at­ives of desoxypi­pra­drol show that they exhibit a cocaine-​​like binding profile (Schmitt et al., 2008).

Cur­rently, there is no known medi­cinal use for this com­pound, although it was ori­gin­ally developed by Ciba-​​Geigy (Novartis) in 1953 to be used to wake patients fol­lowing anaes­thesia (Belucci, 1955).

Desoxypipradrol & Pipradrol

This com­pound is related to pipra­drol, a previously-​​licensed medi­cine for treat­ment of Atten­tion Deficit Hyper­activity Dis­order (ADHD), obesity and nar­co­lepsy. Pipra­drol is clas­si­fied under the Misuse of Drugs Act as a Class C sub­stance. Pipra­drol still used is some coun­tries, but its use is limited due to its abuse poten­tial; it is a dopamine and nore­pineph­rine reup­take inhibitor.

Pipra­drol and its desoxy form have struc­tur­ally related pyrrolidine ana­logues (see below) such as diphen­yl­pro­linol (diphenyl-​​2-​​pyrrolidinylmethanol, D2PM), for which there have been a number of recorded cases of car­di­ovas­cular and neuro­psy­chi­atric tox­icity asso­ci­ated with recre­ational use (Lidder et al., 2008, Wood et al., 2008, Wood et al., 2011), and 2-​​diphenylmethyl-​​pyrrolidine, cur­rently mar­keted, along with D2PM and various ana­logues, as chem­ical reagents for use as chiral cata­lysts in organic syn­thesis (Ber­telsen et al., 2005, Sigma-​​Aldrich, 2007).

ß-phenylmethylamphetamine

The two pairs of mater­ials differ only by the size of the nitrogen-​​containing ring. Diphen­yl­pro­linol and its desoxy form have a five-​​membered (pyrrolidine) ring, while pipra­drol and its desoxy form have a six-​​membered (piperidine) ring. It seems that the two desoxy forms have par­tic­u­larly long-​​lasting effects as their struc­tures are res­istant to meta­bolism, meaning that they have longer half-​​lives in the body. A common feature of these com­pounds is that they are struc­tur­ally related to ß-​​phenylmethylamphetamine, which is also a potent stim­u­lant with a long half life. However, these com­pounds differ from ß-​​phenylmethylamphetamine in that the nitrogen atom is linked to the a– methyl group by two or three carbon atoms to form a ring.

Pipradrol Analogues

Various ana­logues of these com­pounds have been invest­ig­ated and found to have stim­u­lant prop­er­ties (Isbell, 1970 and US Patents). Simple modi­fic­a­tions, for example, addi­tion of halogen, alkyl or alkoxy groups on one or both of the phenyl rings or addi­tion of alkyl, alkenyl, haloalkyl and hydroxyalkyl groups on the nitrogen atom have been reported to produce com­pounds having a stim­u­lant effect on the CNS, which could lead to a range of “designer” forms.

Other modi­fic­a­tions that have been reported in the lit­er­ature include repla­cing the piperidine ring with an azepane ring (7-​​membered ring), a mor­pholine ring or a pyridine ring (Win­throp, 1961; Enyedy, 2003). The piperidine ring has also been mod­i­fied by sub­sti­tu­tion in the ring with an hydroxy group (Nodine, 1960), fusion of the piperidine ring with a benzene ring (Win­throp, 1961) and by sub­sti­tu­tion at the nitrogen atom with an ethano bridge to form a bicyclic ring system (Wiki­pedia, 2011).

Almost all of the ana­logues invest­ig­ated are struc­tur­ally related to the 2-​​isomer of desoxypi­pra­drol, with 2 carbon atoms between the phenyl rings and the nitrogen atom. The only excep­tions being the N–haloalkyl deriv­at­ives of desoxypi­pra­drol and the pyridine ana­logue in which the 2-​​, 3– and 4– isomers were all reported to be active. No examples were found of com­pounds related to 1-​​diphenylmethylpiperidine (N–diphen­yl­methyl– piperidine).

Whilst, it should be pos­sible to dis­tin­guish between pipra­drol isomers using tech­niques such as NMR, in the long term it would be support forensic ana­lysis to have ref­er­ence stand­ards of all the pipra­drol pos­i­tional isomers. The ACMD recom­mends that the Home Office con­siders com­mis­sioning the pro­duc­tion of stand­ards through the Forensic Early Warning System.

2. Use and prevalence

The National Poisons Inform­a­tion Service in Edin­burgh high­lighted that a number of indi­viduals had presented to the Royal Edin­burgh Infirmary in the summer of 2010 fol­lowing their use of desoxypi­pra­drol with symp­toms that were similar to amphet­amine tox­icity, but with pre­dom­inant neuro­psy­chi­atric fea­tures including:

  • Hal­lu­cin­a­tions
  • Para­noia
  • Severe Agit­a­tion

In some patients the symp­toms were still being mani­fested 5 – 7 days after inges­tion and some patients presented dir­ectly to psy­chi­atric ser­vices, bypassing A&E. There were approx­im­ately 12 cases over this period. It was sub­sequently reported that 4 out of 5 of the Edin­burgh cases in whom con­firm­atory tox­ic­o­lo­gical screening was carried out were pos­itive for desoxypi­pra­drol in urine/​blood con­firming exposure.

The number of patients presenting after con­firmed inges­tion of desoxypi­pra­drol after the summer of 2010 has dra­mat­ic­ally reduced in Edin­burgh with no cases in 2011 and data from the National Poisons Inform­a­tion Service (NPIS) sug­gests that there has also been a sig­ni­ficant reduc­tion nation­ally. However, as noted below cases of diphen­yl­pro­linol (D2PM) tox­icity con­tinue to occur.

So far 3 deaths have been linked to the use of desoxypipradrolb(awaiting final reports).

Data provided by the Home Office Centre for Applied Science and Tech­no­logy (CAST) under its Forensic Early Warning System (FEWS) reported one sample of 2-​​DPMP (from a head-​​shop), 10 samples of D2PM and 4 samples of desoxy-​​D2PM (from test pur­chases) during the pilot study.

LGC Forensics reported those samples of “Ivory Wave” it had seen in 2009 – 2011 con­tained dif­ferent active ingredi­ents including the cath­inone MDPV (methyl­e­ne­di­oxypyro­va­lerone) then, after this became con­trolled, naphyrone, and when this too was con­trolled, desoxypi­pra­drol. More recently, diphen­yl­pro­linol has begun to appear in “legal high” products.

Desoxypi­pra­drol has been found as a white powder that is gen­er­ally taken by nasal insuf­fla­tion (sniffing the powder into the nose) or swal­lowing after wrap­ping the powder in a cigar­ette paper (“bombing”) to avoid any unpleasant taste.

It is con­sidered that 2-​​DPMP and its related com­pounds, as cap­tured under the generic defin­i­tion (see recom­mend­a­tion), have poten­tial social harms. It appears to the ACMD that such harms are likely in rela­tion to the impair­ment of func­tion through drug use (mood dis­orders, changes to life­style), loss of rela­tion­ships and the poten­tial harm to others (dir­ectly and indirectly).

3. Preclinical Data

In the 1950’s, Ciba-​​Geigy invest­ig­ated the effects of desoxypi­pra­drol, amphet­amine and d-​​methylamphetamine on small animals (report kindly provided by Novartis). The LD50 is the dose, which kills 50% of the animals:

Table 1. Tox­icity of desoxypi­pra­drol and other com­pounds, meas­ured as LD50, to small animals.

Desoxypi­pra­d­rol
LD50 g/​kg
Amphet­am­ine
LD50 g/​kg
D-​​methylamphetamine
LD50 g/​kg
Mouse iv*0.0200.0500.020
” sc0.0470.0600.080
” po0.0500.0700.150
Rat iv0.0150.0120.023
” sc0.0300.0120.015
” po0.0800.0130.025
Rab­bit iv0.0060.0400.030
” sc0.0070.0450.020
” po0.0800.1700.200

(*iv – intra­venous, sc – sub­cu­taneous, po – orally)Table 1 shows that desoxypi­pra­drol is, in many cases, more toxic than amphet­amine and d-​​methylamphetamine.

The Ciba-​​Geigy report (from the 1950s) also noted that desoxypipradrol:

pro­duced a marked central arousal in various, non-​​anaesthetised animals, con­sisting ini­tially of general agit­a­tion, sub­sequently a greater degree of increase in co-​​ordinated motility, heightened reflexes, com­pelled move­ments and rel­at­ively slight res­pir­atory stimulation.

This was easily dis­cern­ible object­ively in the normal mouse with the aid of the cage move­ment regis­tra­tion method. With this method the indi­vidual move­ments are registered dir­ectly and added up by means of a totaliser.

Figure 1. Effect­ive­ness of desoxypi­pra­drol in stim­u­lating activity in mice when when admin­istered sub­cu­taneously (heavy line) or orally (thin line)
(Figure repro­duced with kind per­mis­sion of Novartis)

The data show that desoxypi­pra­drol is effective as a stim­u­lant in doses com­par­able to those for amphet­amine or methyl­amphet­amine – from 1 mg/​kg upwards. For the pur­poses of its research at the time, Novartis recom­mended an initial human dose of 1mg or less, (ca 0.014 mg/​kg). Anec­dotal inform­a­tion would suggest that the human dose is only a few mg, with 10mg or more being con­sidered harmful.

Exper­i­mental data sup­plied by Dr Colin Dav­idson (St Georges, Uni­ver­sity of London, 2011) demon­strated that desoxypi­pra­drol potently stim­u­lated dopamine release from rat brain slices in vitro. Dopamine release was meas­ured from the region of the nucleus accum­bens, using carbon fibre micro­elec­trodes and fast cyclic voltam­metry to elec­tric­ally measure the oxid­a­tions of dopamine. The rate of recovery of stim­u­lated dopamine release also allowed meas­ure­ment of the action of the drug as an inhib­itor of the dopamine reup­take mech­anism. Dopamine release in the nucleus accum­bens is con­sidered to be a key target for psy­chos­tim­u­lant drugs.

Figure 2. Effect of desoxypi­pra­drol (10uM) on dopamine efflux in rat nucleus accum­bens

It also proved pos­sible to compare the potency of desoxypi­pra­drol with the psy­chos­tim­u­lant drug cocaine in the brain slice pre­par­a­tion. The results (Figure 3) indicate that desoxypi­pra­drol is both more effective and more potent than cocaine in stim­u­lating dopamine release and in inhib­iting its reuptake.

Figure 3. Com­par­ison of poten­cies of desoxypi­pra­drol and cocaine in releasing dopamine, and inhib­iting inac­tiv­a­tion in rat brain slice pre­par­a­tions (C. Dav­idson, unpub­lished)

The results both from Novartis and from Dr Dav­idson indicate that desoxypi­pra­drol is very potent and com­par­able to amphet­amine or methyl­amphet­amine in its poten­tial to cause acute toxicity.

The avail­able human data also show it to be a long-​​lasting sub­stance, capable of eli­citing agit­a­tion lasting for several days after a single dose.

In addi­tion to the reports of tox­icity asso­ci­ated with the use of desoxypi­pra­drol noted above, there have also been reports of sig­ni­ficant tox­icity asso­ci­ated with the recre­ational use of the related com­pound diphen­yl­pro­linol (D2PM). In addi­tion, reports from forensic pro­viders suggest that D2PM has replaced desoxypi­pra­drol in many “Ivory Wave” products. The clin­ical tox­ic­o­logy service at Guy’s and St Thomas’ Hos­pital in London have doc­u­mented 6 cases of ana­lyt­ic­ally con­firmed D2PM tox­icity: 1 case in 2008 and 5 cases in 2010 /​ 2011 (Lidder et al., 2008, Wood et al., 2008, Wood et al., 2011). In these cases patients have presented with a variety of symp­toms including:

  • chest pain
  • agit­a­tion
  • anxiety
  • insomnia
  • hal­lu­cin­a­tions
  • para­noia

In many of these cases patients have had ongoing fea­tures, in par­tic­ular neuro-​​psychiatric fea­tures such as anxiety, insomnia and para­noia for up to 48 – 96 hours after use of D2PM.

4. Recommendation

The ACMD advises that the harms of desoxypi­pra­drol are com­men­surate with other Class B drugs and recom­mend that it is con­trolled under the Misuse of Drugs Act 1971 as a Class B sub­stance and in Schedule 1 of the Misuse of Drugs Reg­u­la­tions 2001 (as amended). Fur­ther­more, we recom­mend that the struc­tur­ally related com­pounds diphen­yl­pro­linol (diphenyl-​​2-​​pyrrolidinyl-​​methanol, D2PM) and its desoxy form 2-​​diphenylmethylpyrrolidine are sim­il­arly con­trolled under the Misuse of Drugs Act 1971 and sched­uled under the Misuse of Drugs Reg­u­la­tions 2001 by virtue of a generic defin­i­tion (see Annex 1 of the report) to ensure that desoxypi­pra­drol and related com­pounds, e.g. diphen­yl­pro­linol, diphen­yl­methyl­pyrrolidine, are fully cap­tured (see Annex 1 & 2).

The ACMD under­stands that desoxypi­pra­drol and its related com­pounds do not have any medi­cinal uses; however, the ACMD has not form­ally con­sulted with the industry.

The pro­posed generic defin­i­tion includes desoxypi­pra­drol and those ana­logues most likely to be pro­duced as altern­at­ives. Some of the com­pounds that fall within the scope of the pro­posed generic defin­i­tion contain a hydroxy group, which can be con­verted to an ester or ether. Such com­pounds may have similar phar­ma­co­lo­gical prop­er­ties to the parent com­pound and there­fore it is recom­mended that esters and ethers of these com­pounds are also subject to control under the Misuse of Drugs Act, 1971.

Whilst, ideally, any generic defin­i­tion would include all pos­sible pos­i­tional isomers, this may mean that non-​​active com­pounds would also be con­trolled. Further, a defin­i­tion to cover all of these poten­tial ana­logues is feas­ible, but it would be very complex and pos­sibly dif­fi­cult to understand.

Under the defin­i­tion that the ACMD propose at Annex 1 esters and ethers of pipra­drol would not be con­trolled. This is because pipra­drol is spe­cific­ally excluded from the generic defin­i­tion and there­fore para­graph 2A would also not apply to pipra­drol. For con­sist­ency the ACMD advise the inclu­sion of esters and ethers of pipra­drol by moving pipra­drol from Schedule 2 Part III para­graph 1(a) to para­graph 1(b) so that para­graph 1(d) regarding esters or ethers would apply to pipradrol.

The ACMD further advise that ste­reoi­somers should be con­trolled by Schedule 2 Part II para­graph 2. The three main drugs, desoxypi­pra­drol, diphen­yl­pro­linol (D2PM) and
2-​​diphenylmethylpyrrolidine all have ste­reoi­somers and most of the com­pounds covered by the generic defin­i­tion will also have stereoisomers.

5. References

  1. Bel­lucci G. (1955); (2-​​Diphenylmethyl-​​piperidine hydro­chloride and the methyl ester of 2-chloro-2-phenyl-2-(2-piperidyl)-acetic acid), drugs with waking effect in anaes­thesia. Minerva Anestesiolo­gica 21: 125 – 8.
  2. Ber­telsen S, Halland N, Bach­mann S, Marigo M, Braunton A, Jør­gensen KA. (2005); Organocata­lytic asym­metric a-​​bromination of alde­hydes and ketones. Chem­ical Com­mu­nic­a­tions 4821 – 4823.
  3. Enyedy IJ, Sakamuri S, Zaman WA, Johnson KM, Wang S. (2003); Pharmacophore-​​based dis­covery of sub­sti­tuted pyridines as novel dopamine trans­porter inhib­itors. Bioor­ganic & Medi­cinal Chem­istry Letters;13:513 – 517.
  4. Hoff­mann K, Heer J. (1958); 2-​​Diphenylmethyl-​​piperidine com­pounds. US Patent 2,826,583.
  5. Hoff­mann K, Heer J. (1958); Piperidines and their man­u­fac­ture. US Patent 2,849,453.
  6. Hoffman K. (1962); 1-​​Ethyl-​​2-​​diphenylmethyl-​​piperidines. US Patent 3,048,594.
  7. Hoff­mann K, Heer J. (1960); Sub­sti­tuted 2-​​diphenylmethyl-​​piperidine com­pounds. US Patent 2,957,879.
  8. Isbell H, Chrus­ciel TS. (1970); Depend­ence Liab­ility of Non-​​Narcotic Drugs. Bul­letin of the World Health Organ­isa­tion; 43: Sup­ple­ment, pages 76 – 77.
  9. Lidder S, Dargan P, Sexton M, Button J, Ramsey J, Holt D, Wood D. (2008); Car­di­ovas­cular tox­icity asso­ci­ated with recre­ational use of diphen­yl­pro­linol (diphenyl-​​2-​​pyrrolidinemethanol [D2PM]). Journal of Medical Tox­ic­o­logy; 4(3):167 – 9.
  10. Nodine JH, Bodi T, Slap J, Levy HA, Siegler PE. (1960); Pre­lim­inary trial of a new stim­u­lant SCH 5472 in ambu­latory patients with depres­sion, exhaus­tion, or hyper­somnia syn­drome. Anti­bi­otic Medi­cine and Clin­ical Therapy ; 7:771 – 6.
  11. Novartis (1955) Inform­a­tion on Prep. No. 14?469 (desoxypi­pra­drol), a new syn­thetic stim­u­lant with central point of application.
  12. Schmitt KC, Zhen J, Kharkar P, Mishra M, Chen N, Dutta AK, Reith ME. (2008); Inter­ac­tion of cocaine-​​, benztropine-​​, and GBR12909-​​like com­pounds with wild-​​type and mutant human dopamine trans­porters: molecular fea­tures that dif­fer­en­tially determine antagonist-​​binding prop­er­ties; Journal of Neuro­chem­istry 107: 928 – 40.
  13. Sigma-​​Aldrich Co. (2007) “Organocata­lysis”, Chem­istry files, vol 7, No.
  14. Wiki­pedia entry for AL-​​1095. <http://​en​.wiki​pedia​.org/​w​i​k​i​/​A​L​-​1​095>; 2011 [accessed 25.08.11].
  15. Win­throp SO. (1960) a-(3-Morpholyl)-benzhydrol and its salts. US Patent 2,947,749.
  16. Win­throp SO. (1961); 3-​​Benzhydrylmorpholine and salts thereof, and method of pre­paring said com­pounds. US Patent 2,993,895.
  17. Win­throp SO, Humber LG. (1961); Central Stim­u­lants. Cyc­lized Diphen­yl­iso­p­ro­pyl­am­ines. Journal of Organic Chem­istry 26: 2834 – 6.
  18. Wood DM, Davies S, Puchnarewicz, Holt DW, Dargan PI. A case series of indi­viduals with ana­lyt­ic­ally con­firmed acute diphenyl-​​2– pyrrolid­ine­meth­anol (D2PM) tox­icity. Manu­script sub­mitted for publication.
  19. Wood DM, Puchnarewicz M, Holt DW, Ramsey J, Dargan PI. (2011); Detec­tion of the pre­cursor ben­zo­phenone in indi­viduals who have used legal highs con­taining diphenyl-​​2-​​pyyrrolidinemethanol (D2PM). Basic & Clin­ical Phar­ma­co­logy & Tox­ic­o­logy; 109 (Suppl. 1): 86.

Annex 1

Proposed generic definition

Any com­pound (not being pipra­drol) struc­tur­ally derived from piperidine, pyrrolidine, azepane, mor­pholine or pyridine by sub­sti­tu­tion on a ring carbon atom with a diphen­yl­methyl group, whether or not the com­pound is further mod­i­fied in any of the fol­lowing ways, that is to say,

  1. by sub­sti­tu­tion in any of the phenyl rings to any extent with alkyl, alkoxy, haloalkyl or halide groups;
  2. by sub­sti­tu­tion on the methyl carbon atom with an alkyl, hydroxyalkyl or hydroxy group;
  3. by sub­sti­tu­tion on the ring nitrogen atom with an alkyl, alkenyl, haloalkyl or hydroxyalkyl group.

One Response to Ivory Wave Destined For Class B

  1. Mike says:

    How sad. You’d think after the cata­strophic failure of both Alcohol Pro­hib­i­tion and 30 years of self-​​destructive drug wars, they’d learn that the more they ban some­thing the more it is desired and spread throughout a pop­u­la­tion. Want to stop people from doing it? Make it the most boring thing in the world. The Neth­er­lands handily accom­plished this having numerous, boring, drawn-​​out sem­inars and classes in school about heroine, and then made it avail­able by pre­scrip­tion at hos­pital clinics. Heroine use as a result plummeted 50% in the teenage pop­u­la­tion. Why? Because they made it BORING, not taboo.

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