Meptazinol

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−1
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.^[1] 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.^[2]

^ US patent 4197239, Cavalla JF, Shepherd RG, White AC, "Hexahydroazepine, Piperidine and Pyrrolidine Derivatives", issued 1980-04-08, assigned to Wyeth
^ 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.

[1] US patent 4197239, Cavalla JF, Shepherd RG, White AC, "Hexahydroazepine, Piperidine and Pyrrolidine Derivatives", issued 1980-04-08, assigned to Wyeth

[Holmes_1985-2] 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.

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