meptazinol

{{Short description|Opioid analgesic drug}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 462248630

| IUPAC_name = (RS)-3-(3-Ethyl-1-methylazepan-3-yl)phenol

| image = Meptazinol.svg

| image_class = skin-invert-image

| width = 150

| chirality = Racemic mixture

| tradename = Meptid

| Drugs.com = {{drugs.com|international|meptazinol}}

| licence_EU =

| licence_US =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU = Schedule 4

| legal_CA =

| legal_UK = POM

| legal_US =

| legal_status =

| dependency_liability = Low

| routes_of_administration = By mouth, intramuscular, intravenous

| bioavailability =

| protein_bound =

| 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

| class = Opioid

| index2_label = HCl

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 54340-58-8

| CAS_number2_Ref = {{cascite|correct|CAS}}

| CAS_number2 = 59263-76-2

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 18Y7S5JKZD

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = T62FQ4ZCPA

| ATC_prefix = N02

| ATC_suffix = AX05

| ATC_supplemental =

| PubChem = 41049

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 37469

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D08182

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 314437

| C = 15

| H = 23

| N = 1

| O = 1

| smiles = OC1=CC=CC(C2(CCCCN(C2)C)CC)=C1

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = JLICHNCFTLFZJN-UHFFFAOYSA-N

| synonyms =

| density =

| melting_notes =

| boiling_point =

| solubility =

| specific_rotation =

| sec_combustion =

}}

Meptazinol, sold under the brand name Meptid, is an opioid analgesic developed by Wyeth in the 1970s.{{ cite patent | country = US | status = patent | number = 4197239 | title = Hexahydroazepine, Piperidine and Pyrrolidine Derivatives | gdate = 1980-04-08 | inventor = Cavalla JF, Shepherd RG, White AC | assign1 = Wyeth }} 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.{{ cite journal |vauthors=Holmes B, Ward A | title = Meptazinol. A Review of its Pharmacodynamic and Pharmacokinetic Properties and Therapeutic Efficacy | journal = Drugs | year = 1985 | volume = 30 | issue = 4 | pages = 285–312 | pmid = 2998723 | doi=10.2165/00003495-198530040-00001| s2cid = 208818234 }}