# Chloromorphide

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Chloromorphide
> Markdown URL: https://mediated.wiki/source/Chloromorphide.md
> Source: https://en.wikipedia.org/wiki/Chloromorphide
> Source revision: 1330779691
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Short description|Opiate analog and derivative of morphine}}{{One source|date=March 2023}}{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 423378340
| IUPAC_name = 3-Hydroxy-6α-chloro-7,8-didehydro-4,5α-epoxy-17-methylmorphinan
| image = Chloromorphide.svg
| image_class = skin-invert-image
| width = 180

<!--Clinical data-->
| tradename =  
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B            / C / D / X -->
| pregnancy_category =  
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!--             / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL         / P       / POM / CD / Class A, B, C -->
| legal_US =  
| legal_status =  
| routes_of_administration =

<!--Pharmacokinetic data-->
| bioavailability =  
| protein_bound =  
| metabolism =  
| elimination_half-life =  
| excretion =

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 63783-53-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Q35VX87X79
| ATC_prefix = none
| ATC_suffix =  
| PubChem = 5745724
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =  
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4676779
| synonyms = α-Chloromorphide

<!--Chemical data-->
| C=17 | H=18 | Cl=1 | N=1 | O=2 
| smiles = Cl[C@H]2\C=C/[C@H]5[C@@H]4N(CC[C@@]51c3c(O[C@H]12)c(O)ccc3C4)C
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C17H18ClNO2/c1-19-7-6-17-10-3-4-11(18)16(17)21-15-13(20)5-2-9(14(15)17)8-12(10)19/h2-5,10-12,16,20H,6-8H2,1H3/t10-,11-,12+,16-,17-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = URUOTSLJEBANHA-ZFDIKFDDSA-N
}}

'''Chloromorphide''' ('''α-chloromorphide''') is an [opiate](/source/opiate) [analog](/source/structural_analog) that is a derivative of [morphine](/source/morphine), where the 6-hydroxy group has been replaced by chlorine. Developed in 1933 in Germany, it has approximately ten times the potency of morphine.<ref>{{cite journal | vauthors = ((Yeh HJC)), Wilson RS, Klee WA, Jacobson AE | journal = J Pharm Sci | year = 1976 | volume = 65 | pages = 902–4 | doi = 10.1002/jps.2600650624 | pmid = 932978 | title = Alpha-and beta-halomorphides: Stereochemistry, analgesic potency, toxicity, and interaction with narcotic receptors in vitro | issue = 6}}</ref> It has similar effects to morphine, such as [sedation](/source/sedation), [analgesia](/source/analgesia), and [respiratory depression](/source/respiratory_depression).

Chloromorphide does not appear specifically in the Controlled Substances Act 1970 in the United States, but is presumably Schedule II controlled substance as a form of [morphine](/source/morphine) or an analogue of morphine or morphinan. When halogenated morphides and codides are used for research or industrial uses, they are often synthesised on-site.

Chloromorphide is one of a series of opioids known as morphides and codides, which are important precursors and intermediates in the synthesis of semi-synthetic opioid analgesic drugs, especially those with additions, substitutions, or other modifications at the 7, 8, and/or 14 positions on the morphine carbon skeleton. Semisynthetics with changes at other positions can also be made from these compounds. The codeine analog of chloromorphide is [α-chlorocodide](/source/%CE%B1-chlorocodide) (alpha-chlorcodide), an intermediate in one method of [desomorphine](/source/desomorphine) synthesis which uses [codeine](/source/codeine) as precursor.

During the 1930s, the entire series of alpha- and beta-halogenated codides, morphides, dihydromorphides, and dihydrocodides were produced and described,{{citation needed|date=February 2013}} and α-bromomorphide and α-iodomorphide are sometimes currently used in research and manufacturing.{{citation needed|date=February 2013}}

==References==
{{Reflist|2}}

{{Opioidergics}}

Category:4,5-Epoxymorphinans
Category:Organochlorides
Category:Hydroxyarenes
Category:Mu-opioid receptor agonists
Category:Semisynthetic opioids

---
Adapted from the Wikipedia article [Chloromorphide](https://en.wikipedia.org/wiki/Chloromorphide) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Chloromorphide?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.