Diacetyldihydromorphine

Diacetyldihydromorphine

Systematic (IUPAC) name
(5α,6α)-7,8-Dihydro- 4,5-epoxy- 17-methylmorphinan- 3,6-diacetate
Clinical data
Pregnancy cat.	?
Legal status	Schedule I (US)
Routes	Intravenous
Identifiers
CAS number	509-71-7
ATC code	None
PubChem	CID 5359460
ChemSpider	4514291 Y
Synonyms	Diacetyldihydromorphine, Paralaudin, Dihydroheroin, Acetylmorphinol
Chemical data
Formula	C21H25NO5
Mol. mass	371.427 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C21H25NO5/c1-11(23)25-16-6-4-13-10-15-14-5-7-17(26-12(2)24)20-21(14,8-9-22(15)3)18(13)19(16)27-20/h4,6,14-15,17,20H,5,7-10H2,1-3H3/t14-,15+,17-,20-,21-/m0/s1 Y Key:NCXVKLDKUADJPV-PVHGPHFFSA-N Y
Y(what is this?)  (verify)

Diacetyldihydromorphine (paralaudin, dihydroheroin, acetylmorphinol) is a potent opiate derivative developed in Germany in 1929 which is rarely used in some countries for the treatment of severe pain such as that caused by terminal cancer, as a more potent form of diamorphine (also commonly known as Heroin). Diacetyldihydromorphine is fast acting and longer lasting than diamorphine, with a duration of action of around 4-7 hours.^[1]

Diacetyldihydromorphine is quickly metabolized by plasma esterase enzymes into dihydromorphine, in the same way that diacetylmorphine is metabolized into morphine; however unlike dihydromorphine, which is more potent than morphine on a mg to mg basis, diacetyldihydromorphine is actually less potent than diamorphine, perhaps because it is metabolized more slowly. Diacetyldihydromorphine is approximately equipotent to morphine whereas diamorphine is 1.50-1.80 times the potency of morphine.^[2] It shares with other opioids the risk of overdose or (potentially life-threatening) respiratory depression. When strong narcotics are required, and morphine and diamorphine are not an option, it is more common to use better known drugs such as nicomorphine, hydromorphone, levorphanol, oxymorphone or fentanyl which doctors will be more familiar with, and which do not share the stigma associated with either heroin or morphine. Side effects are similar to those of other semi-synthetic opiates and fully synthetic opioids, and the most commonly reported side effects include drowsiness, nausea, and constipation. Compared to morphine, diacetyldihydromorphine produces far fewer side effects which are also often lower in intensity. Though the two drugs are very similar in effects, morphine often produces more intense side effects, including euphoria, constipation, miosis, physical dependence, psychological dependence, potentially life-threatening respiratory depression, and a severe addiction.

References

1. ^ Gilbert, AK; Hosztafi, S; Mahurter, L; Pasternak, GW (2004). "Pharmacological characterization of dihydromorphine, 6-acetyldihydromorphine and dihydroheroin analgesia and their differentiation from morphine". European journal of pharmacology 492 (2-3): 123–30. doi:10.1016/j.ejphar.2004.03.050. PMID 15178355. 
2. ^ Martin, WR; Fraser, HF (1961). "A comparative study of physiological and subjective effects of heroin and morphine administered intravenously in postaddicts". The Journal of pharmacology and experimental therapeutics 133: 388–99. PMID 13767429.