Chloromorphide

Chloromorphide (α-chloromorphide) is an opiate analog that is a derivative of morphine, where the 6-hydroxy group has been replaced by chlorine.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
Clinical data
Other namesα-Chloromorphide
ATC code
  • none
Identifiers
IUPAC name
  • 3-Hydroxy-6α-chloro-7,8-didehydro-4,5α-epoxy-17-methylmorphinan
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H18ClNO2
Molar mass303.79 g·mol−1
3D model (JSmol)
SMILES
  • Cl[C@H]2\C=C/[C@H]5[C@@H]4N(CC[C@@]51c3c(O[C@H]12)c(O)ccc3C4)C
InChI
  • InChI=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 N
  • Key:URUOTSLJEBANHA-ZFDIKFDDSA-N N
 NY (what is this?)  (verify)

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 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 (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, and α-bromomorphide and α-iodomorphide are sometimes currently used in research and manufacturing.

References
  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.
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