Meptazinol

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

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 Y HCl: 59263-76-2 Y
PubChem CID	41049
ChemSpider	37469 Y
UNII	18Y7S5JKZD HCl: T62FQ4ZCPA Y
KEGG	D08182 Y
ChEMBL	ChEMBL314437 Y
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 Y Key:JLICHNCFTLFZJN-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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]

Review:^[3]