Chloromorphide

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Chloromorphide
Chloromorphide.svg
Systematic (IUPAC) name
3-Hydroxy-6α-chloro-7,8-didehydro-4,5α-epoxy-17-methylmorphinan
Clinical data
Legal status ?
Identifiers
CAS number 63783-53-9 YesY
ATC code None
PubChem CID 5745724
ChemSpider 4676779 N
Synonyms α-Chloromorphide
Chemical data
Formula C17H18ClNO2 
Mol. mass 303.78 g/mol
 N (what is this?)  (verify)

Chloromorphide (α-chloromorphide) is an opiate analog that is a derivative of morphine, where the 6-hydroxy group has been replaced by chlorine.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.[1] It has similar effects to morphine such as sedation, analgesia and respiratory depression.

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 position 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 (alphachlorcodide), an intermediate in one method of desomorphine synthesis which uses 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] and α-bromomorphide and α-iodomorphide are sometimes currently used in research and manufacturing.[citation needed]

References[edit]

  1. ^ Yeh HJC, Wilson RS, Klee WA, Jacobson AE (1976). "Alpha-and beta-halomorphides: Stereochemistry, analgesic potency, toxicity, and interaction with narcotic receptors in vitro". J Pharm Sci 65 (6): 902–4. doi:10.1002/jps.2600650624. PMID 932978.