Meptazinol

Meptazinol
Clinical data
Trade namesMeptid
AHFS/Drugs.comInternational Drug Names
Dependence
liability
Low
Routes of
administration
By mouth, intramuscular, intravenous
Drug classOpioid
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
Pharmacokinetic data
MetabolismThe peak analgesic effect is seen within 30–60 minutes and lasts about 3–4 hours
Elimination half-lifeHalf-life (1.4–4 hours)
ExcretionThe drug is rapidly metabolized to the glucuronide, and mostly excreted in the urine
Identifiers
  • (RS)-3-(3-Ethyl-1-methylazepan-3-yl)phenol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.053.718 Edit this at Wikidata
Chemical and physical data
FormulaC15H23NO
Molar mass233.355 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • OC1=CC=CC(C2(CCCCN(C2)C)CC)=C1
  • InChI=1S/C15H23NO/c1-3-15(9-4-5-10-16(2)12-15)13-7-6-8-14(17)11-13/h6-8,11,17H,3-5,9-10,12H2,1-2H3 checkY
  • Key:JLICHNCFTLFZJN-UHFFFAOYSA-N checkY
 X markNcheckY (what is this?)  (verify)

Meptazinol, sold under the brand name Meptid, is an opioid analgesic developed by Wyeth in the 1970s. Indications for use in moderate to severe pain, most commonly used to treat pain in obstetrics (childbirth).

Meptazinol is a 3-phenylazepane derivative, whereas the other phenazepanes like ethoheptazine and proheptazine are 4-phenylazepanes.

A partial μ-opioid receptor agonist, its mixed agonist/antagonist activity affords it a lower risk of dependence and abuse than full μ agonists like morphine. Meptazinol exhibits not only a short onset of action, but also a shorter duration of action relative to other opioids such as morphine, pentazocine, or buprenorphine.

Meserine is a carbamate derivative of meptazinol.

Chemical structure of meserine

References

  1. ↑ US patent 4197239, Cavalla JF, Shepherd RG, White AC, "Hexahydroazepine, Piperidine and Pyrrolidine Derivatives", issued 1980-04-08, assigned to Wyeth
  2. ↑ Holmes B, Ward A (1985). "Meptazinol. A Review of its Pharmacodynamic and Pharmacokinetic Properties and Therapeutic Efficacy". Drugs. 30 (4): 285–312. doi:10.2165/00003495-198530040-00001. PMID 2998723. S2CID 208818234.
  3. ↑ CID 73330571 from PubChem
  4. ↑ Zhang H, Wang Y, Wang Y, Li X, Wang S, Wang Z (October 2022). "Recent advance on carbamate-based cholinesterase inhibitors as potential multifunctional agents against Alzheimer's disease". European Journal of Medicinal Chemistry. 240 114606. doi:10.1016/j.ejmech.2022.114606. PMID 35858523.