gemazocine

{{short description|Chemical compound}}

{{Drugbox

| IUPAC_name = 10-(cyclopropylmethyl)-1-ethyl-13,13-dimethyl-10-azatricyclo[7.3.1.0^2,7]trideca-2,4,6-trien-4-ol

| image = Gemazocine structure.svg

| CAS_number = 54063-47-7

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

| UNII = V1A2S0LB62

| ATC_prefix = None

| ATC_suffix =

| PubChem = 219096

| ChemSpiderID = 189916

| ChEMBL = 2105066

| C = 20 | H = 29 | N = 1 | O = 1

| smiles = Oc1ccc4c(c1)C2(C(C(N(CC2)CC3CC3)C4)(C)C)CC

| StdInChI = 1S/C20H29NO/c1-4-20-9-10-21(13-14-5-6-14)18(19(20,2)3)11-15-7-8-16(22)12-17(15)20/h7-8,12,14,18,22H,4-6,9-11,13H2,1-3H3

| StdInChIKey = AFZOCGNTFCGOEE-UHFFFAOYSA-N

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| pregnancy_category =

| legal_status =

| routes_of_administration =

}}

Gemazocine (R-15,497), also known as cyclogemine, is a non-selective opioid antagonist of the benzomorphan class.{{ cite book | vauthors = Macdonald F | title = Dictionary of Pharmacological Agents | url = https://books.google.com/books?id=DeX7jgInYFMC&pg=PA955 | access-date = 22 April 2012 | year = 1997 | publisher = CRC Press | isbn = 978-0-412-46630-4 | page = 955 }}{{ cite journal | title = Structural Studies of Substituted 6,7-Benzomorphan Compounds. I. The Absolute Configuration of (−)-2-Cyclopropylmethyl-2'-hydroxy-5-ethyl-9,9-dimethyl-6,7-benzomorphan (Gemazocine) Hydrobromide | vauthors = Gelders YG, de Ranter CJ, Schenk H | journal = Acta Crystallographica B | year = 1979 | volume = 35 | issue = 3 | pages = 699–703 | doi = 10.1107/S0567740879004477 | bibcode = 1979AcCrB..35..699G | url = http://scripts.iucr.org/cgi-bin/paper?S0567740879004477 | url-access = subscription }}{{cite journal | vauthors = Verlinde C, De Ranter C | title = Assessment of the kappa-opioid activity of a series of 6,7-benzomorphans in the rabbit vas deferens | journal = European Journal of Pharmacology | volume = 153 | issue = 1 | pages = 83–87 | date = August 1988 | pmid = 2850928 | doi = 10.1016/0014-2999(88)90590-0 }} It may have partial agonist properties at some of the opioid receptors, such as at the kappa receptor (as it induces dysphoric effects in humans), but seems to be generally antagonistic in its actions.{{cite journal | vauthors = Freye E, Hartung E, Schenk GK | title = Bremazocine: an opiate that induces sedation and analgesia without respiratory depression | journal = Anesthesia and Analgesia | volume = 62 | issue = 5 | pages = 483–488 | date = May 1983 | pmid = 6301311 | doi = 10.1213/00000539-198305000-00005 | doi-access = free }}