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Meptazinol

Clinical data
Trade names	Meptid
AHFS/Drugs.com	International Drug Names
Dependence liability	Low
Routes of administration	By mouth, intramuscular, intravenous
Drug class	Opioid
ATC code	N02AX05 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only)
Pharmacokinetic data
Metabolism	The peak analgesic effect is seen within 30–60 minutes and lasts about 3–4 hours
Elimination half-life	Half-life (1.4–4 hours)
Excretion	The drug is rapidly metabolized to the glucuronide, and mostly excreted in the urine
Identifiers
IUPAC name (RS)-3-(3-Ethyl-1-methylazepan-3-yl)phenol
CAS Number	54340-58-8 HCl: 59263-76-2
PubChem CID	41049
ChemSpider	37469
UNII	18Y7S5JKZD HCl: T62FQ4ZCPA
KEGG	D08182
ChEMBL	ChEMBL314437
CompTox Dashboard (EPA)	DTXSID6048543
ECHA InfoCard	100.053.718
Chemical and physical data
Formula	C15H23NO
Molar mass	233.355 g·mol
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
SMILES OC1=CC=CC(C2(CCCCN(C2)C)CC)=C1
InChI 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 Key:JLICHNCFTLFZJN-UHFFFAOYSA-N
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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.

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.

External links

• Meptazinol at the U.S. National Library of Medicine Medical Subject Headings (MeSH)

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