Noracymethadol

Noracymethadol (INN) is a synthetic opioid analgesic related to methadone that was never marketed.[1] In a clinical trial of postpartum patients it was reported to produce analgesia comparable to that of morphine but with less nausea, dizziness, and drowsiness.[2][3] Other side effects included salivation, ataxia, and respiratory depression that was reversible by naloxone.[2][3] Similarly to many of its analogues, noracymethadol is a Schedule I controlled substance in the United States with an ACSCN of 9633 and 2013 annual manufacturing quota of 12 grammes. [4] and is also controlled internationally under the United Nations Single Convention on Narcotic Drugs of 1961.[5] The salts known are the gluconate (free base conversion ratio 0.633) and hydrochloride (0.903).

Noracymethadol
Clinical data
ATC code
  • None
Legal status
Legal status
  • CA: Schedule I
  • DE: Anlage I (Authorized scientific use only)
  • US: Schedule I
Identifiers
IUPAC name
  • 6-(Methylamino)-4,4-diphenyl-3-heptanyl acetate
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard100.014.571
Chemical and physical data
FormulaC22H29NO2
Molar mass339.479 g·mol−1
3D model (JSmol)
SMILES
  • O=C(OC(C(c1ccccc1)(c2ccccc2)CC(NC)C)CC)C
InChI
  • InChI=1S/C22H29NO2/c1-5-21(25-18(3)24)22(16-17(2)23-4,19-12-8-6-9-13-19)20-14-10-7-11-15-20/h6-15,17,21,23H,5,16H2,1-4H3
  • Key:VWCUGCYZZGRKEE-UHFFFAOYSA-N

Noracymethadol is an acetyl ester of methadol and it can be said with some precision that it is either the heroin or 6-monoacetylmorphine analogue of methadol, and being a methadol it exhibits optical isomerism. The other methadols (acetylmethadol, methadol &c) have at least four optical isomers (see Orlaam).

See also

References
  1. Macdonald F (21 November 1996). Dictionary of Pharmacological Agents. CRC Press. p. 1447. ISBN 978-0-412-46630-4. Retrieved 11 May 2012.
  2. Gruber CM, Baptisti A (1963). "Estimating the acceptability of morphine and noracymethadol in postpartum patients". Clinical Pharmacology and Therapeutics. 4 (2): 172–81. doi:10.1002/cpt196342172. PMID 13950878. S2CID 19919842.
  3. Lister RE (June 1966). "The toxicity of some of the newer narcotic analgesics". The Journal of Pharmacy and Pharmacology. 18 (6): 364–83. doi:10.1111/j.2042-7158.1966.tb07890.x. PMID 4381372. S2CID 32896981.
  4. "Controlled Substances in Schedule I". Drug Enforcement Administration - Office of Diversion Control. Retrieved 2012-05-11.
  5. Nordegren T (1 March 2002). The A-Z Encyclopedia of Alcohol and Drug Abuse. Universal-Publishers. p. 468. ISBN 978-1-58112-404-0. Retrieved 11 May 2012.
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