AH-7921

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AH-7921
AH-7921 structure.png
Systematic (IUPAC) name
3,4-dichloro-N-[(1-dimethylamino)cyclohexylmethyl]benzamide
Identifiers
CAS Registry Number 55154-30-8 N
ATC code None
PubChem CID: 187760
ChemSpider 163208 YesY
Synonyms AH-7921
Chemical data
Formula C16H22Cl2N2O
Molecular mass 329.265 g/mol
 N (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] It was discovered in the 1970s[3] by a team at Allen and Hanburys.

Dosages have been reported to range from as little as 10 mg to around 200 mg or higher (for opioid-tolerant individuals).[citation needed] This would confirm the previous studies of AH-7921 being roughly 80% as potent as morphine.[citation needed]

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.[4]

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Standard for the Uniform Scheduling of Medicines and Poisons) in Australia in May 2014.[5] Although this amendment was repealed in June 2014,[6] which simply means the amendment document ceases, but the actual scheduling is permanent as part of the main document (all SUSMP amendments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.[7]

In the UK, AH-7921 was included as a Class A drug under the 1971 Act in January 2015.[8]

In Brazil, it's considered an illegal drug since May 2015. [9]

Synthesis[edit]

AH-7921 U.S. Patent 3,975,443 (1976). Harper et al. 1976.

See also[edit]

References[edit]

  1. ^ Brittain, R. T.; Kellett, D. N.; Neat, M. L.; Stables, R. (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. (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. ^ US patent 3975443, Harper, N.; Veitch, G., "1-(3,4-DICHLOROBENZAMIDOMETHYL)-CYCLOHEXYLDIMETHYLAMINE", issued 1976-08-17, assigned to Allen & Hanburys 
  4. ^ Uchiyama, N.; Matsuda, S.; Kawamura, M.; Kikura-Hanajiri, R.; Goda, Y. (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. doi:10.1007/s11419-013-0182-9. 
  5. ^ http://www.tga.gov.au/pdf/scheduling/scheduling-decisions-1405-final.pdf
  6. ^ http://www.comlaw.gov.au/Details/F2014L00566
  7. ^ http://www.health.gov.il/LegislationLibrary/Homarim-12092013.pdf
  8. ^ https://www.gov.uk/government/publications/circular-0012015-a-change-to-the-misuse-of-drugs-act-1971-control-of-ah-7921-lsd-related-compounds-tryptamines-and-rescheduling-of-ghb/circular-0012015-a-change-to-the-misuse-of-drugs-act-1971-control-of-ah-7921-lsd-related-compounds-tryptamines-and-rescheduling-of-ghb
  9. ^ http://portal.anvisa.gov.br/wps/wcm/connect/5887f100485fb8f3b2d8bb734e60b39c/44+-+RDC+n%C2%BA+18-2015-DOU.pdf?MOD=AJPERES