Substituted amphetamine

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Substituted amphetamines
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Substituted amphetamine
Chemical class
Substituted derivatives of amphetamine
Legal status
In Wikidata
Optical isomers of amphetamine
L-amphetamine D-amphetamine

Substituted amphetamines are a

DOM
(STP).

Some of amphetamine's substituted

empathogenic
. Various substituted amphetamines may cause these actions either separately or in combination.

Partial list of substituted amphetamines

Generic or Trivial Name Chemical Name # of Subs
Amphetamine α-Methyl-phenethylamine 0
Methamphetamine N-Methylamphetamine 1
Ethylamphetamine N-Ethylamphetamine 1
Propylamphetamine N-Propylamphetamine 1
Isopropylamphetamine N-iso-Propylamphetamine 1
Phentermine α-Methylamphetamine 1
Phenylpropanolamine (PPA) β-Hydroxyamphetamine, (1R,2S)- 1
Cathine β-Hydroxyamphetamine, (1S,2S)- 1
Cathinone β-Ketoamphetamine 1
Ortetamine 2-Methylamphetamine 1
2-Fluoroamphetamine (2-FA) 2-Fluoroamphetamine 1
3-Methylamphetamine (3-MA) 3-Methylamphetamine 1
2-Phenyl-3-aminobutane 2-Phenyl-3-aminobutane 1
Tranylcypromine Trans-2-phenylcyclopropylamine  
3-Fluoroamphetamine (3-FA) 3-Fluoroamphetamine 1
Norfenfluramine 3-Trifluoromethylamphetamine 1
4-Methylamphetamine (4-MA) 4-Methylamphetamine 1
para-Methoxyamphetamine (PMA) 4-Methoxyamphetamine 1
para-Ethoxyamphetamine 4-Ethoxyamphetamine 1
4-Methylthioamphetamine (4-MTA) 4-Methylthioamphetamine 1
Norpholedrine
(α-Me-TRA)
4-Hydroxyamphetamine 1
para-Bromoamphetamine (PBA, 4-BA) 4-Bromoamphetamine 1
para-Chloroamphetamine (PCA, 4-CA) 4-Chloroamphetamine 1
para-Fluoroamphetamine
(PFA, 4-FA, 4-FMP)
4-Fluoroamphetamine 1
para-Iodoamphetamine (PIA, 4-IA) 4-Iodoamphetamine 1
Clobenzorex N-(2-chlorobenzyl)-1-phenylpropan-2-amine 1
Dimethylamphetamine N,N-Dimethylamphetamine 2
Benzphetamine N-Benzyl-N-methylamphetamine 2
D-Deprenyl N-Methyl-N-propargylamphetamine, (S)- 2
Selegiline N-Methyl-N-propargylamphetamine, (R)- 2
Mephentermine N-Methyl-α-methylamphetamine 2
Phenpentermine
α,β-Dimethylamphetamine 2
Ephedrine β-Hydroxy-N-methylamphetamine, (1R,2S)- 2
Pseudoephedrine (PSE) β-Hydroxy-N-methylamphetamine, (1S,2S)- 2
Methcathinone β-Keto-N-methylamphetamine 2
Ethcathinone β-Keto-N-ethylamphetamine 2
Clortermine 2-Chloro-α-methylamphetamine 2
Methoxymethylamphetamine
(MMA)
3-Methoxy-4-methylamphetamine 2
Fenfluramine 3-Trifluoromethyl-N-ethylamphetamine 2
Dexfenfluramine 3-Trifluoromethyl-N-ethylamphetamine, (S)- 2
4-Methylmethamphetamine
(4-MMA)
4-Methyl-N-methylamphetamine 2
para-Methoxymethamphetamine
(PMMA)
4-Methoxy-N-methylamphetamine 2
para-Methoxyethylamphetamine
(PMEA)
4-Methoxy-N-ethylamphetamine 2
Pholedrine 4-Hydroxy-N-methylamphetamine 2
Chlorphentermine 4-Chloro-α-methylamphetamine 2
para-Fluoromethamphetamine
(PFMA, 4-FMA)
4-Fluoro-N-methylamphetamine 2
Xylopropamine 3,4-Dimethylamphetamine 2
α-Methyldopamine (α-Me-DA) 3,4-Dihydroxyamphetamine 2
3,4-Methylenedioxyamphetamine (MDA) 3,4-Methylenedioxyamphetamine 2
Dimethoxyamphetamine (DMA) X,X-Dimethoxyamphetamine 2
6-APB 6-(2-aminopropyl)benzofuran 2
Nordefrin
(α-Me-NE)
β,3,4-Trihydroxyamphetamine, (R)- 3
Oxilofrine β,4-Dihydroxy-N-methylamphetamine 3
Aleph 2,5-dimethoxy-4-methylthioamphetamine 3
Dimethoxybromoamphetamine
(DOB)
2,5-Dimethoxy-4-bromoamphetamine 3
Dimethoxychloroamphetamine
(DOC)
2,5-Dimethoxy-4-chloroamphetamine 3
Dimethoxyfluoroethylamphetamine
(DOEF)
2,5-Dimethoxy-4-fluoroethylamphetamine 3
Dimethoxyethylamphetamine
(DOET)
2,5-Dimethoxy-4-ethylamphetamine 3
Dimethoxyfluoroamphetamine
(DOF)
2,5-Dimethoxy-4-fluoroamphetamine 3
Dimethoxyiodoamphetamine
(DOI)
2,5-Dimethoxy-4-iodoamphetamine 3
Dimethoxymethylamphetamine
(DOM)
2,5-Dimethoxy-4-methylamphetamine 3
Dimethoxynitroamphetamine
(DON)
2,5-Dimethoxy-4-nitroamphetamine 3
Dimethoxypropylamphetamine
(DOPR)
2,5-Dimethoxy-4-propylamphetamine 3
Dimethoxytrifluoromethylamphetamine
(DOTFM)
2,5-Dimethoxy-4-trifluoromethylamphetamine 3
Methylenedioxymethamphetamine (MDMA) 3,4-Methylenedioxy-N-methylamphetamine 3
Methylenedioxyethylamphetamine
(MDEA)
3,4-Methylenedioxy-N-ethylamphetamine 3
Methylenedioxyhydroxyamphetamine
(MDOH)
3,4-Methylenedioxy-N-hydroxyamphetamine 3
2-Methyl-MDA 3,4-Methylenedioxy-2-methylamphetamine 3
5-Methyl-MDA 4,5-Methylenedioxy-3-methylamphetamine 3
Methoxymethylenedioxyamphetamine
(MMDA)
3-Methoxy-4,5-methylenedioxyamphetamine 3
Trimethoxyamphetamine (TMA) X,X,X-Trimethoxyamphetamine 3
Dimethylcathinone
β-Keto-N,N-dimethylamphetamine 3
Diethylcathinone
β-Keto-N,N-diethylamphetamine 3
Bupropion β-Keto-3-chloro-N-tert-butylamphetamine 3
Mephedrone (4-MMC) β-Keto-4-methyl-N-methylamphetamine 3
Methedrone (PMMC) β-Keto-4-methoxy-N-methylamphetamine 3
Brephedrone
(4-BMC)
β-Keto-4-bromo-N-methylamphetamine 3
Flephedrone (4-FMC) β-Keto-4-fluoro-N-methylamphetamine 3

Prodrugs of amphetamine/methamphetamine

A variety of

Structure

This shows phenethylamine in blue with its substitution points marked. Amphetamine and its substituted derivatives contain a CH3 group at the alpha-position (Rα).
NH2 group
which is unmarked. The wavy line between α carbon and CH3 group indicates isomerism; the CH3 group may either be towards or away from the viewer.

Amphetamines are a subgroup of the

methyl and sometimes ethyl groups at the amine and phenyl sites:[8][9][10]

Substance Substituents Structure Sources
N α β phenyl group
2 3 4 5
Phenethylamine Phenethylamine
Amphetamine (α-methylphenylethylamine) -CH3 Amphetamine [7]
Methamphetamine (N-methylamphetamine) -CH3 -CH3 Methamphetamine [7]
Phentermine (α-methylamphetamine) -(CH3)2 Phentermine [7]
Ephedrine -CH3 -CH3 -OH (+)-Ephedrine [7]
Pseudoephedrine -CH3 -CH3 -OH (+)-Pseudoephedrine [7]
Cathinone -CH3 =O Cathinone [7]
Methcathinone (ephedrone) -CH3 -CH3 =O Methcathinone [7]
MDA (3,4-methylenedioxyamphetamine) -CH3 -O-CH2-O- 3,4-methylenedioxyamphetamine [7]
MDMA (3,4-methylenedioxymethamphetamine) -CH3 -CH3 -O-CH2-O- 3,4-methylenedioxymethamphetamine [7]
MDEA
(3,4-methylenedioxy-N-ethylamphetamine)
-CH2-CH3 -CH3 -O-CH2-O- methylenedioxyethylamphetamine [7]
EDMA (3,4-ethylenedioxy-N-methylamphetamine) -CH3 -CH3 -O-CH2-CH2-O- 3,4-ethylenedioxy-N-methylamphetamine
MBDB (N-methyl-1,3-benzodioxolylbutanamine) -CH3 -CH2-CH3 -O-CH2-O- N-methyl-1-(3,4-methylenedioxyphenyl)-2-aminobutane
PMA (para-methoxyamphetamine) -CH3 -O-CH3 para-methoxyamphetamine
PMMA
(para-methoxymethamphetamine)
-CH3 -CH3 -O-CH3 para-methoxymethamphetamine
4-MTA
(4-methylthioamphetamine)
-CH3 -S-CH3 4-methylthioamphetamine
3,4-DMA (3,4-dimethoxyamphetamine) -CH3 -O-CH3 -O-CH3 dimethoxyamphetamine
3,4,5-Trimethoxyamphetamine (α-methylmescaline) -CH3 -O-CH3 -O-CH3 -O-CH3 trimethoxyamphetamine
DOM
(2,5-dimethoxy-4-methylamphetamine)
-CH3 -O-CH3 -CH3 -O-CH3 2,5-dimethoxy-4-methylamphetamine
DOB (2,5-dimethoxy-4-bromoamphetamine) -CH3 -O-CH3 -Br -O-CH3 2,5-dimethoxy-4-bromoamphetamine

History

norephedrine (phenylpropanolamine) and norpseudoephedrine (cathine). Natives of Yemen and Ethiopia have a long tradition of chewing khat leaves to achieve a stimulating effect. The active substances of khat are cathinone and, to a lesser extent, cathine.[11]

Benzedrine) for colds and nasal congestion. Subsequently, amphetamine was used in the treatment of narcolepsy, obesity, hay fever, orthostatic hypotension, epilepsy, Parkinson's disease, alcoholism and migraine.[12][15] The "reinforcing" effects of substituted amphetamines were quickly discovered, and the misuse of substituted amphetamines had been noted as far back as 1936.[15]

Amphetamine pills

During World War II, amphetamines were used by the German military to keep their tank crews awake for long periods, and treat depression. It was noticed that extended rest was required after such artificially induced activity.[12] The widespread use of substituted amphetamines began in postwar Japan and quickly spread to other countries. Modified "designer amphetamines", such as MDA and PMA, have gained in popularity since the 1960s.[15] In 1970, the United States adopted "the Controlled Substances Act" that limited non-medical use of substituted amphetamines.[15] Street use of PMA was noted in 1972.[16] MDMA emerged as a substitute for MDA in the early 1970s.[17] American chemist Alexander Shulgin first synthesized the drug in 1976 and through him the drug was briefly introduced into psychotherapy.[18] Recreational use grew and in 1985 MDMA was banned by the US authorities in an emergency scheduling initiated by the Drug Enforcement Administration.[19]

Since the mid-1990s, MDMA has become a popular

entactogenic drug among the youth and quite often non-MDMA substances were sold as ecstasy.[20] Ongoing trials are investigating its efficacy as an adjunct to psychotherapy in the management of treatment-resistant post-traumatic stress disorder (PTSD).[21]

Legal status

Agents Legal status by 2009.[22][23][24][25]
US Russia Australia
racemic
)
Schedule II Schedule II Schedule II Schedule 8
Dextroamphetamine (D-amphetamine) Schedule II Schedule II Schedule I Schedule 8
Levoamphetamine (L-amphetamine) Schedule II Schedule II Schedule III Schedule 8
Methamphetamine Schedule II Schedule II Schedule I Schedule 8
Cathinone Methcathinone Schedule I Schedule I Schedule I Schedule 9
MDEA
Schedule I Schedule I Schedule I Schedule 9
PMA Schedule I Schedule I Schedule I Schedule 9
Schedule I Schedule I Schedule I Schedule 9

See also

References

  1. ^
    PMID 22502775
    . Substituted amphetamines, which are also called phenylpropylamino alkaloids, are a diverse group of nitrogen-containing compounds that feature a phenethylamine backbone with a methyl group at the α-position relative to the nitrogen (Figure 1). Countless variation in functional group substitutions has yielded a collection of synthetic drugs with diverse pharmacological properties as stimulants, empathogens and hallucinogens [3]. ... Beyond (1R,2S)-ephedrine and (1S,2S)-pseudoephedrine, myriad other substituted amphetamines have important pharmaceutical applications. The stereochemistry at the α-carbon is often a key determinant of pharmacological activity, with (S)-enantiomers being more potent. For example, (S)-amphetamine, commonly known as d-amphetamine or dextroamphetamine, displays five times greater psychostimulant activity compared with its (R)-isomer [78]. Most such molecules are produced exclusively through chemical syntheses and many are prescribed widely in modern medicine. For example, (S)-amphetamine (Figure 4b), a key ingredient in Adderall and Dexedrine, is used to treat attention deficit hyperactivity disorder (ADHD) [79]. ...
    [Figure 4](b) Examples of synthetic, pharmaceutically important substituted amphetamines.
  2. ^ . The simplest unsubstituted phenylisopropylamine, 1-phenyl-2-aminopropane, or amphetamine, serves as a common structural template for hallucinogens and psychostimulants. Amphetamine produces central stimulant, anorectic, and sympathomimetic actions, and it is the prototype member of this class (39).
  3. .
  4. .
  5. .
  6. .
  7. ^ . Retrieved 16 February 2019.
  8. ^ Goldfrank, pp. 1125–1127
  9. ^ Glennon, pp. 184–187
  10. ^ Schatzberg, p.843
  11. .
  12. ^ a b c Snow, p. 1
  13. S2CID 1786307
    .
  14. ^ Goldfrank, p. 1125
  15. ^ a b c d Goldfrank, p. 1119
  16. from the original on 26 November 2009.
  17. ^ Foderaro, Lisa W. (11 December 1988). "Psychedelic Drug Called Ecstasy Gains Popularity in Manhattan Nightclubs". The New York Times. Archived from the original on 17 November 2015. Retrieved 27 August 2015.
  18. PMID 20653618
    .
  19. ^ Snow, p. 71
  20. ^ Goldfrank, p. 1121
  21. PMID 20643699
    .
  22. ^ "List of psychotropic substances under international control" (PDF). International Narcotics Control Board. August 2003. Archived from the original on 25 November 2010.{{cite web}}: CS1 maint: unfit URL (link) May 2010 Edition Archived 24 December 2012 at the Wayback Machine
  23. ^ "DEA Drug Scheduling". U.S. Drug Enforcement Administration. Archived from the original on 7 February 2011. Retrieved 17 November 2009.
  24. ^ "Resolution of RF Government of 30 June 1998 N 681 "On approval of list of drugs psychotropic substances and their precursors subject to control in the Russian Federation"". garant.ru (in Russian). Archived from the original on 20 January 2012. Retrieved 15 November 2009.
  25. ^ "The Standard for the Uniform Scheduling of Medicines and Poisons (SUSMP)". Australian Therapeutic Goods Administration (TGA). Archived from the original on 27 June 2015. Retrieved 26 June 2015.
  26. ^ "Convention on Psychotropic Substances, 1971" (PDF). United Nations. Archived from the original on 25 November 2010.{{cite web}}: CS1 maint: unfit URL (link)

Bibliography

External links