AH-7921

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AH-7921
AH-7921 structure.svg
Systematic (IUPAC) name
3,4-dichloro-N-{[1-(dimethylamino)cyclohexyl]methyl}benzamide
Legal status
Legal status
Identifiers
CAS Number 55154-30-8 YesY
ATC code none
PubChem CID 187760
ChemSpider 163208 YesY
UNII 10BR7A0SO0
Synonyms AH-7921
Chemical data
Formula C16H22Cl2N2O
Molar mass 329.265 g/mol
 NYesY (what is this?)  (verify)

AH-7921 is an opioid analgesic drug selective for the µ-opioid receptor, having around 80% the potency of morphine when administered orally.[1][2][3] It was discovered in the 1970s[4] by a team at Allen and Hanburys.

Use[edit]

Although AH-7921 was extensively studied in vitro and in animals, though not in humans, by the developing company, it was never sold commercially for medical use. In 2013, AH-7921 was discovered to have been used as an active ingredient in "synthetic cannabis" products in Japan.[5] In October 2015, two horses (Bossmon and Literata) trained by owner-trainer Roy Sedlacek tested positive for AH-7921 at Belmont Park racetrack.[6]

Legality[edit]

AH-7921 was made a Prohibited Substance (Schedule 9 of the Standard for the Uniform Scheduling of Medicines and Poisons) in Australia in May 2014.[7] Although this amendment was repealed in June 2014,[8] which simply means the amendment document ceases, but the actual scheduling is permanent as part of the main document (all SUSMP amendments cease after a few weeks). It may, however, still be a banned import.

AH-7921 has been illegal to distribute in Israel since December 2013.[9]

In the UK, AH-7921 was included as a Class A drug under the 1971 Act in January 2015 as part of the Misuse of Drugs Act 1971 (Amendment) (No. 2) Order 2014.[10]

In Brazil, AH-7921 has been considered an illegal drug since May 2015.[11]

As of October 2015 AH-7921 is a controlled substance in China.[12]

AH-7921 is banned in the Czech Republic.[13]

In the United States, AH-7921 was placed into Schedule I of the Controlled Substances Act on May 16, 2016.[14]

See also[edit]

References[edit]

  1. ^ Brittain, R. T.; Kellett, D. N.; Neat, M. L.; Stables, R. (September 1973). "Proceedings: Anti-nociceptive effects in N-substituted cyclohexylmethylbenzamides". British Journal of Pharmacology 49 (1): 158P–159P. doi:10.1111/j.1476-5381.1973.tb08279.x. PMC 1776456. PMID 4207044. 
  2. ^ Hayes, A. G.; Tyers, M. B. (July 1983). "Determination of receptors that mediate opiate side effects in the mouse". British Journal of Pharmacology 79 (3): 731–736. doi:10.1111/j.1476-5381.1983.tb10011.x. PMC 2044905. PMID 6317119. 
  3. ^ N. J. Harper; G. B. A. Veitch; D. G. Wibberley (November 1974). "1-(3,4-Dichlorobenzamidomethyl)cyclohexyldimethylamine and related compounds as potential analgesics". Journal of Medicinal Chemistry 17 (11): 1188–1193. doi:10.1021/jm00257a012. PMID 4416926. 
  4. ^ US patent 3975443, Harper, N.; Veitch, G., "1-(3,4-DICHLOROBENZAMIDOMETHYL)-CYCLOHEXYLDIMETHYLAMINE", issued 1976-08-17, assigned to Allen & Hanburys 
  5. ^ Nahoko Uchiyama; Satoru Matsuda; Maiko Kawamura; Ruri Kikura-Hanajiri; Yukihiro Goda (July 2013). "Two new-type cannabimimetic quinolinyl carboxylates, QUPIC and QUCHIC, two new cannabimimetic carboxamide derivatives, ADB-FUBINACA and ADBICA, and five synthetic cannabinoids detected with a thiophene derivative α-PVT and an opioid receptor agonist AH-7921 identified in illegal products". Forensic Toxicology 31 (2): 223–240. doi:10.1007/s11419-013-0182-9. 
  6. ^ "Two horses test positive for designer drug". Racing Post. Retrieved 29 April 2016. 
  7. ^ Final decisions and reasons for decisions by delegates of the Secretary to the Department of Health
  8. ^ Poisons Standard Amendment No. 2 of 2014
  9. ^ פקודת הסמים המסוכנים נוסח חדש, תשל"ג-1973
  10. ^ The Misuse of Drugs Act 1971 (Amendment) (No. 2) Order 2014
  11. ^ Resolução da Diretoria Colegiada - RDC nº 87 de 28/06/2016
  12. ^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Retrieved 1 October 2015. 
  13. ^ "Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.)" (PDF) (in Czech). Ministerstvo zdravotnictví. 
  14. ^ "Schedules of Controlled Substances: Placement of AH-7921 Into Schedule I". Drug Enforcement Administration. 14 April 2016.