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Chloromorphide (α-chloromorphide) is an opiate analog that is a derivative of morphine, where the 6-hydroxy group has been replaced by chlorine.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 names	α-Chloromorphide
ATC code	none
Identifiers
IUPAC name 3-Hydroxy-6α-chloro-7,8-didehydro-4,5α-epoxy-17-methylmorphinan
CAS Number	63783-53-9 Y
PubChem CID	5745724
ChemSpider	4676779 N
UNII	Q35VX87X79
CompTox Dashboard (EPA)	DTXSID90213223
Chemical and physical data
Formula	C17H18ClNO2
Molar mass	303.79 g·mol−1
3D model (JSmol)	Interactive image
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 (alpha-chlorcodide), 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]}