AH-7921

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AH-7921
AH-7921 structure.png
Systematic (IUPAC) name
3,4-dichloro-N-[(1-dimethylamino)cyclohexylmethyl]benzamide
Clinical data
Legal status
?
Identifiers
CAS number 55154-30-8 N
ATC code None
PubChem CID 187760
ChemSpider 163208 YesY
Synonyms AH-7921
Chemical data
Formula C16H22Cl2N2O 
Mol. 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). This would confirm the previous studies of AH-7921 being roughly 80% as potent as morphine.[citation needed]

Use[edit]

A trivial name(s) doxylam has been proposed for this compound, but it has never been 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for the Uniform Scheduling of Medicines and Poisons) in Australia in May 2014.[5] Although this amendment has been repealed as of 02 Jun 2014.[6] which simply means the amendment document ceases, but the actual scheduling is permanent as part of the main document [all SUSMP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.

Illegal to distribute in Israel since 12.9.2013[7]

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. PMC 1776456. PMID 4207044.  edit
  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.  edit
  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.  edit
  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