Diacetyldihydromorphine

Title: Diacetyldihydromorphine
CAS Registry Number: 509-71-7
CAS Name: (5a,6a)-4,5-Epoxy-17-methylmorphinan-3,6-diol diacetate (ester)
Additional Names: dihydroheroin; paralaudin
Molecular Formula: C21H25NO5
Molecular Weight: 371.43
Percent Composition: C 67.91%, H 6.78%, N 3.77%, O 21.54%
Literature References: Prepn from dihydromorphine: Eddy, Howes, J. Pharmacol. 53, 430 (1935); Small, Mallonee, J. Org. Chem. 12, 558-566 (1947); K. W. Bentley, The Chemistry of the Morphine Alkaloids (Oxford, 1954).
Properties: Needles, mp 165-167°. Slightly sol in water; sol in chloroform, alcohol, ether.
Melting point: mp 165-167°
Derivative Type: Hydrochloride
Molecular Formula: C21H25NO5.HCl
Molecular Weight: 407.89
Percent Composition: C 61.84%, H 6.42%, N 3.43%, O 19.61%, Cl 8.69%
Properties: Flakes, scales. mp 215-218°. [a]D29 -59° (c = 1.2). Very sol in water.
Melting point: mp 215-218°
Optical Rotation: [a]D29 -59° (c = 1.2)
Diacetylmorphine Diafenthiuron Dialifor Diallate Diallyl Trisulfide

Diacetyldihydromorphine
Dihydroheroin.svg
Systematic (IUPAC) name
(5α,6α)-7,8-Dihydro-4,5-epoxy-17-methylmorphinan 3,6-diacetate
Clinical data
Legal status Schedule I (US)
Routes Intravenous
Identifiers
CAS number 509-71-7 YesY
ATC code None
PubChem CID 5359460
ChemSpider 4514291 YesY
Synonyms Diacetyldihydromorphine, Paralaudin, Dihydroheroin, Acetylmorphinol
Chemical data
Formula C21H25NO5 
Mol. mass 371.427 g/mol
 YesY (what is this?)  (verify)

Diacetyldihydromorphine (also known as paralaudin, dihydroheroin or 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 diamorphine 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 of diacetyldihydromorphine 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.