cyprodime

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 410884288

| IUPAC_name = (–)-N-(Cyclopropylmethyl)-4,14-dimethoxymorphinan-6-one

| image = Cyprodime.svg

| image_class = skin-invert-image

| alt = Structural formula

| width = 200

| image2 = Cyprodime molecule ball.png

| alt2 = Ball-and-stick model

| width2 = 210

| tradename =

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

| CAS_number = 118111-54-9

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

| UNII = 2C6F5L8S8X

| ATC_prefix = none

| ATC_suffix =

| PubChem = 5748293

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

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| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 322796

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 20133376

| smiles = O=C4CC[C@@]3(OC)[C@@H]2N(CC[C@]3(c1c(cccc1OC)C2)C4)CC5CC5

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C22H29NO3/c1-25-18-5-3-4-16-12-19-22(26-2)9-8-17(24)13-21(22,20(16)18)10-11-23(19)14-15-6-7-15/h3-5,15,19H,6-14H2,1-2H3/t19-,21-,22+/m0/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = INUCRGMCKDQKNA-ILWGZMRPSA-N

| C=22 | H=29 | N=1 | O=3

| synonyms = Cyprodime

}}

Cyprodime is an opioid antagonist from the morphinan family of drugs.

Cyprodime is a selective opioid antagonist which blocks the μ-opioid receptor,{{cite journal | vauthors = Schmidhammer H, Burkard WP, Eggstein-Aeppli L, Smith CF | title = Synthesis and biological evaluation of 14-alkoxymorphinans. 2. (-)-N-(cyclopropylmethyl)-4,14-dimethoxymorphinan-6-one, a selective mu opioid receptor antagonist | journal = Journal of Medicinal Chemistry | volume = 32 | issue = 2 | pages = 418–21 | date = February 1989 | pmid = 2536439 | doi = 10.1021/jm00122a021 }} but without affecting the δ-opioid or κ-opioid receptors. This makes it useful for scientific research as it allows the μ-opioid receptor to be selectively deactivated so that the actions of the δ and κ receptors can be studied separately, in contrast to better known opioid antagonists such as naloxone which block all three opioid receptor subtypes.{{cite journal | vauthors = Márki A, Monory K, Otvös F, Tóth G, Krassnig R, Schmidhammer H, Traynor JR, Roques BP, Maldonado R, Borsodi A | display-authors = 6 | title = Mu-opioid receptor specific antagonist cyprodime: characterization by in vitro radioligand and [35S]GTPgammaS binding assays | journal = European Journal of Pharmacology | volume = 383 | issue = 2 | pages = 209–14 | date = October 1999 | pmid = 10585536 | doi = 10.1016/s0014-2999(99)00610-x }}