Systematic (IUPAC) name

4,5--Epoxy-17-methylmorphinan-3-ol
Clinical data
Trade names Permonid
Legal status Prohibited (S9) (AU) Class
A (UK) Schedule I (US)
Dependence liability Very High
Identiers
CAS number
427-00-9
ATC code None
PubChem CID 5362456
ChemSpider
4515044
UNII
7OP86J5E33
ChEMBL
CHEMBL2106274
Synonyms Desomorphine,
Dihydrodesoxymorphine,
Permonid
Chemical data
Formula
C
17
H
21
NO
2
Mol. mass 271.354 g/mol
Desomorphine
Desomorphine
From Wikipedia, the free encyclopedia
Desomorphine (dihydrodesoxymorphine,
former brand name Permonid, street name
krokodil) is a derivative of morphine with
powerful, fast-acting opioid eects, such as
sedation and analgesia.
[1][2][3][4]
First
synthesized in 1932 and patented in 1934,
[5]
desomorphine was used in Switzerland
under the brand name Permonid
[6]
and was
described as having a fast onset and a short
duration of action, with relatively little
nausea or respiratory depression compared
to equivalent doses of morphine.
Dose-by-dose it is eight to ten times more
potent than morphine.
[7]
Desomorphine is derived from morphine
where the 6-hydroxyl group and the 7,8
double bond have been reduced.
[5]
The
traditional synthesis of desomorphine starts
from -chlorocodide, which is itself
obtained by reacting thionyl chloride with
codeine. By catalytic reduction,
-chlorocodide gives dihydrodesoxycodeine,
which yields desomorphine on
demethylation.
[8][9]
Contents
1 Medical uses
2 Abuse liability
3 Toxicity
4 Physical and chemical properties
5 History
6 Society and culture
6.1 Recreational use
6.2 Western media coverage
6.3 Street prices
7 References
SMILES
InChI
Desomorphine - Wikipedia, the free encyclopedia https://en.wikipedia.org/wiki/Desomorphine
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(what is this?) (verify) Medical uses
It was previously used in Switzerland for the treatment of severe pain; although for many
years up to 1981, when its use was terminated, it was being used to treat a single person
in Bern, Switzerland with a rare illness.
[10]
Abuse liability
Test subjects were subjected to desomorphine intake. The completed tests on animal
subjects produced results that contrast desomorphine to morphine. Compared to
morphine, the results show increased toxicity, more potent relief of pain, higher levels of
depression, increased respiration, and increased digestive activity. Early medical trials of
humans taking desomorphine have resulted in the nding that small amounts are highly
addictive. As of 2013, there are no legal uses of desomorphine in the U.S., where it has
been a Schedule 1 controlled substance since 1936.
[11]
Toxicity
Desomorphine typically has large amounts of toxic substances due to it being "cooked"
and used without any signicant eort to remove the byproducts and leftovers from
synthesis. Injecting any such mixture can cause serious damage of the skin, blood vessels,
bone and muscles, sometimes requiring limb amputation in long-term users.
[7]
Causes of
this damage are from iodine and phosphorus (and other toxic substances) that are present
after synthesis. The large volume of tissue damage/infection is what gained the drug its
nickname of the esh-eating drug.
[12]
Gangrene, phlebitis, thrombosis (blood clots),
pneumonia, meningitis, septicaemia (blood infection), rotting bones, osteomyelitis (bone
infection), liver & kidney damage, brain damage and HIV are also common amongst users
of desomorphine.
[13]
Sometimes, the user will miss the vein when injecting the
desomorphine, creating abscess and causing death of the esh surrounding the entry-
point.
[7]
Physical and chemical properties
Desomorphine has a molecular weight of 271.35 g/mol and three salts are used:
hydrobromide (free-base conversion ratio 0.770), hydrochloride (0.881) and sulfate
(0.802).
[14]
Its freebase form is slightly soluble in water (1.425 g/L at 25 C), although its
salts are very water soluble; its freebase form is also very soluble in most polar organic
solvents (like acetone, ethanol and ethyl acetate).
[7]
Its melting point is 189C.
[7]
It has a
pK
a
of 9.69.
[7]
Desomorphine is made from codeine mixed with other substances. The codeine is
retrieved from over-the-counter medicine and is then mixed with alcohol, gasoline, red
phosphorus, iodine, hydrochloric acid and paint thinner.
[7]
Toxic nitrogen oxides fumes
emerge from the drug when heated.
[15]
Desomorphine - Wikipedia, the free encyclopedia https://en.wikipedia.org/wiki/Desomorphine
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History
Desomorphine was rst synthesised in the U.S. in 1932 and patented on November 13,
1934.
[10]
In Russia, desomorphine was declared an illegal narcotic analgesic in 1998.
However, while codeine-containing drugs generally have been prescription products in
Europe, in Russia they were sold freely over-the-counter until June 2012.
[16]
The number
of users in Russia was estimated to have reached around one million at the peak of the
drug's popularity.
[17]
Society and culture
Recreational use
Desomorphine abuse in Russia attracted international attention in 2010 due to an
increase in clandestine production, presumably due to its relatively simple synthesis from
codeine available over-the-counter. Abuse of homemade desomorphine was rst reported
in Siberia in 2003 when Russia started a major crackdown on heroin production and
tracking, but has since spread throughout Russia and the neighboring former Soviet
republics.
[18]
The drug can be made from codeine and iodine derived from OTC medications and red
phosphorus from match strikers,
[19]
in a process similar to the manufacture of
methamphetamine from pseudoephedrine. Like methamphetamine, desomorphine made
this way is often contaminated with various agents. The street name in Russia for
homemade desomorphine is krokodil (Russian: , crocodile), possibly related to
the chemical name of the precursor -chlorocodide, or similarity of a skin, damaged by the
drug use, to crocodile leather.
[10]
Due to diculties in procuring heroin, combined with
easy and cheap access to over-the-counter pharmacy products containing codeine in
Russia, use of krokodil has increased.
[13]
It has been estimated that around 100,000
people use krokodil in Russia and around 20,000 in Ukraine.
[13]
One death in Poland in
December 2011 was also believed to have been caused by krokodil use, and its use has
been conrmed among Russian expatriate communities in a number of other European
countries.
[20]
Western media coverage
The media in the U.S. and Canada have brought awareness to desomorphine. There have
been incidents reported where desomorphine had supposedly been present within either
country but all incidents have not been conrmed by any drug-testing reports.
[21]
Street prices
In 2011, a study showed that 120 Rubles worth of desomorphine is enough to equal 500
Rubles worth of heroin.
[12]
Desomorphine - Wikipedia, the free encyclopedia https://en.wikipedia.org/wiki/Desomorphine
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Wikimedia Commons has
media related to
Desomorphine.
References
^ Casy, Alan F.; Partt,
Robert T. (1986). Opioid
analgesics: chemistry
and receptors. New
York: Plenum Press.
p. 32.
ISBN 978-0-306-42130-
3.
1.
^ Bognar, R; Makleit, S
(1958). "Neue Methode
fr die Vorbereitung
von dihydro-
6-desoxymorphine"
[New method for the
preparation of dihydro-
6-desoxymorphine].
Arzneimittel-Forschung
(in German) 8 (6):
3235. PMID 13546093
(https://www.ncbi.nlm.
nih.gov/pubmed
/13546093).
2.
^ Janssen, Paul A. J.
(1962). "A Review of
the Chemical Features
Associated with Strong
Morphine-Like
Activity". British
Journal of Anaesthesia
34 (4): 2608.
doi:10.1093/bja
/34.4.260
(http://dx.doi.org
/10.1093%2Fbja%2F34
.4.260).
PMID 14451235
(https://www.ncbi.nlm.
nih.gov/pubmed
/14451235).
3.
^ Sargent, Lewis J.;
May, Everette L.
(1970). "Agonists-
antagonists derived
from desomorphine
and metopon". Journal
of Medicinal Chemistry
13 (6): 10613.
doi:10.1021/jm00300a
009 (http://dx.doi.org
/10.1021%2Fjm00300a
009). PMID 4098039
(https://www.ncbi.nlm.
nih.gov/pubmed
/4098039).
4.
^
a b
US patent
1980972
(http://worldwide.espa
cenet.com
/textdoc?DB=EPODOC
&IDX=US1980972),
Lyndon Frederick
Small, "Morphine
Derivative and
Processes", published
1934-19-07, issued
1934-13-11
5.
^ "Krokodil"
(http://www.oasas.ny.g
ov/AdMed
/FYI/Krokodil.cfm).
New York State Oce
of Alcoholism and
Substance Abuse
Services.
6.
Desomorphine - Wikipedia, the free encyclopedia https://en.wikipedia.org/wiki/Desomorphine
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^
a b c d e f g
Katselou, M; Papoutsis, I;
Nikolaou, P; Spiliopoulou, C; Athanaselis, S
(May 2014). "A "Krokodil" emerges from
the murky waters of addiction. Abuse
trends of an old drug.". Life Sciences 102
(2): 8187. doi:10.1016/j.lfs.2014.03.008
(http://dx.doi.org
/10.1016%2Fj.lfs.2014.03.008).
PMID 24650492
(https://www.ncbi.nlm.nih.gov/pubmed
/24650492).
7.
^ Mosettig, Erich; Cohen, Frank L.; Small,
Lyndon F. (1932). "Desoxycodeine Studies.
III. The Constitution of the So-Called
-Dihydrodesoxycodeine:
Bis-Dihydrodesoxycodeine". Journal of the
American Chemical Society 54 (2): 793801.
doi:10.1021/ja01341a051
(http://dx.doi.org
/10.1021%2Fja01341a051).
8.
^ Eddy, Nathan B.; Howes, Homer A.
(1935). "Studies of Morphine, Codeine and
their Derivatives X. Desoxymorphine-C,
Desoxycodeine-C and their Hydrogenated
Derivatives" (http://jpet.aspetjournals.org
/content/55/3/257.short). Journal of
Pharmacology and Experimental
Therapeutics 55 (3): 25767.
9.
^
a b c
Gahr, M; Freudenmann, RW; Hiemke,
C; Gunst, IM; Connemann, BJ; Schnfeldt-
Lecuona, C (2012). "Desomorphine goes
"crocodile".". Journal of Addictive Diseases
31 (4): 40712.
doi:10.1080/10550887.2012.735570
(http://dx.doi.org
/10.1080%2F10550887.2012.735570).
PMID 23244560
(https://www.ncbi.nlm.nih.gov/pubmed
/23244560).
10.
^ "DESOMORPHINE
(Dihydrodesoxymorphine;
dihydrodesoxymorphine-D; Street Name:
Krokodil, Crocodil"
(http://www.deadiversion.usdoj.gov
/drug_chem_info/desomorphine.pdf).
Drug Enforcement Administration.
Retrieved 3 April 2014.
11.
^
a b
"Desomorphine (Krokodil) Basics"
(http://www.erowid.org/chemicals
/desomorphine
/desomorphine_basics.shtml). Erowid.
Retrieved 3 April 2014.
12.
^
a b c
Grund JP, Latypov A, Harris M
(2013). "Breaking worse: The emergence
of krokodil and excessive injuries among
people who inject drugs in Eurasia".
International Journal of Drug Policy 24 (4):
265274.
doi:10.1016/j.drugpo.2013.04.007
(http://dx.doi.org
/10.1016%2Fj.drugpo.2013.04.007).
PMID 23726898
(https://www.ncbi.nlm.nih.gov/pubmed
/23726898).
13.
^ "Permonid"
(http://pubchem.ncbi.nlm.nih.gov
/summary/summary.cgi?cid=5362456).
PubChem Compound. National Library of
Medicine. Retrieved 5 May 2014.
14.
^ "Desomorphine"
(http://toxnet.nlm.nih.gov/cgi-bin
/sis/search
/a?dbs+hsdb:@term+@DOCNO+8070).
Specialized Information Services.
Retrieved 3 April 2014.
15.
^ . (23 June 2011). "
"
(http://www.gazeta.ru/social/2011/06
/23/3673229.shtml). Gazeta.ru. Retrieved
12 January 2014.
16.
Desomorphine - Wikipedia, the free encyclopedia https://en.wikipedia.org/wiki/Desomorphine
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^ "Krokodil" (http://www.oasas.ny.gov
/AdMed/FYI/Krokodil.cfm). New York State
Oce of Alcoholism and Substance Abuse
Services. Retrieved 3 April 2014.
17.
^ Gahr, M; Freudenmann, C; Hiemke, C;
Gunst, IM; Connemann, BJ; Schnfeldt-
Lecuona, Carlos (2012). "Desomorphine
goes "crocodile" ". Journal of Addictive
Diseases 31 (4): 40712.
doi:10.1080/10550887.2012.735570
(http://dx.doi.org
/10.1080%2F10550887.2012.735570).
PMID 23244560
(https://www.ncbi.nlm.nih.gov/pubmed
/23244560).
18.
^ Savchuk, S. A.; Barsegyan, S. S.;
Barsegyan, I. B.; Kolesov, G. M. (2011).
"Chromatographic study of expert and
biological samples containing
desomorphine". Journal of Analytical
Chemistry 63 (4): 36170.
doi:10.1134/S1061934808040096
(http://dx.doi.org
/10.1134%2FS1061934808040096).
19.
^ Skowronek R, Celiski R, Chowaniec C
(2012). " "Crocodile" new dangerous
designer drug of abuse from the East".
Clinical Toxicology 50 (4): 269.
doi:10.3109/15563650.2012.660574
(http://dx.doi.org
/10.3109%2F15563650.2012.660574).
PMID 22385107
(https://www.ncbi.nlm.nih.gov/pubmed
/22385107).
20.
^ No Conrmed Reports of Desomorphine (
"Krokodil" / "Crocodile" ) in Canada
(http://www.ccsa.ca/Resource%20Library
/ccsa-CCENDU-Desomorphine-Bulletin-
2013-en.pdf). Canadian Centre on
Substance Abuse. November 21, 2013.
ISBN 978-1-77178-052-0.
21.
Retrieved from "http://en.wikipedia.org/w/index.php?title=Desomorphine&
oldid=617235932"
Categories: 1932 introductions Addictive drugs Analgesics Morphinans
Mu-opioid agonists Opioids Phenols Semisynthetic opioids
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