Levorphanol

Structural formula
General
Non-proprietary name	Levorphanol
other names	17-methylmorphinan-3-ol ( IUPAC ) ; (-) - 9a-Methylmorphinan-3-ol-hydrogen tartrate dihydrate; 17-methyl-3-morphinanol; (-) - 3-Hydroxy- N -methylmorphinan; Levorphan; Lemoran;
Molecular formula	C 17 H 23 NO • C 4 H 6 O 6 • 2 H 2 O
Brief description	White or almost white, crystalline powder (tartrate dihydrate)
External identifiers / databases
EC number	201-002-6
ECHA InfoCard	100,000,912
PubChem	5359272
ChemSpider	16736212
DrugBank	DB00854
Wikidata	Q2579108
Drug information
Drug class	Opioid - analgesic
properties
Molar mass	443.50 g · mol -1 (levorphanol)
Melting point	198-199 ° C ; 113–115 ° C (tartrate dihydrate);
solubility	soluble in water and ether, practically insoluble in chloroform (tartrate dihydrate)
safety instructions
H and P phrases	H: 301-312-317-332-334-360
	P: 201-261-280-301 + 310-308 + 313
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Levorphanol is a fully synthetic opioid with a strong analgesic effect. Levorphanol is a pure agonist on the μ-opioid receptor .

pharmacology

effect

As an opioid, levorphanol has the same profile of effects and side effects, and thus essentially the same risk potential as other opioids. Levorphanol has an analgesic potency of 3–5. The increased effect is also associated with an increase in undesirable effects (ADRs, side effects). The dextrorotatory isomer has practically no analgesic activity. Levorphanol is as effective when administered orally as when used parenterally. The ( R, R ) -hydrogen tartrate dihydrate is also used.

Side effects

Side effects can occur with levorphanol that exceed the pre-existing tolerance to opioids due to previous consumption. These are tiredness, sleep disturbances , drowsiness , nausea , vomiting , edema in the legs, urinary retention , constipation and pruritus . They usually go away as tolerance develops or the dose is reduced. Sleep and sexual disorders last the longest . Use during pregnancy and lactation: Levorphanol has an effect on the fetus when taken during pregnancy.

Trade names

Monopreparations : Dromoran.

literature

Hermann PT Ammon et al .: Hunnius Pharmaceutical Dictionary . 9th edition, Walter de Gruyter Verlag , Berlin - New York, 2004, ISBN 3-11-017475-8 geb. and ISBN 3-11-017487-1 brosch., p. 904.
Römpp Lexikon Chemie , Georg Thieme Verlag , Stuttgart - New York, 1997, p. 2398.
THE MERCK INDEX, 15th edition, The Royal Society of Chemistry 2013, ISBN 978-1-84973-670-1 , p. 1017.

Individual evidence

↑ ^a ^b ^c Herman H. Waldvogel: Analgesics Antinociceptives Adjuvants Manual for Pain Practice . Springer-Verlag, 2013, ISBN 978-3-642-56710-0 , pp. 287 ( limited preview in Google Book search).
^ ^A ^b J. Elks: The Dictionary of Drugs: Chemical Data Chemical Data, Structures and Bibliographies . Springer, 2014, ISBN 978-1-4757-2085-3 , pp. 656 ( limited preview in Google Book search).
↑ ^a ^b Data sheet Levorphanol (+) - tartrate salt dihydrate, white powder, ≥98% (HPLC) from Sigma-Aldrich , accessed on July 3, 2016 ( PDF ).
^ Richard Lawrence Miller: The Encyclopedia of Addictive Drugs . Greenwood Publishing Group, 2002, ISBN 978-0-313-31807-8 , pp. 223 ( limited preview in Google Book search).

[Herman_H._Waldvogel-1] Herman H. Waldvogel: Analgesics Antinociceptives Adjuvants Manual for Pain Practice . Springer-Verlag, 2013, ISBN 978-3-642-56710-0 , pp. 287 ( limited preview in Google Book search).

[J._Elks-2] A ^b J. Elks: The Dictionary of Drugs: Chemical Data Chemical Data, Structures and Bibliographies . Springer, 2014, ISBN 978-1-4757-2085-3 , pp. 656 ( limited preview in Google Book search).

[Sigma-3] Data sheet Levorphanol (+) - tartrate salt dihydrate, white powder, ≥98% (HPLC) from Sigma-Aldrich , accessed on July 3, 2016 ( PDF ).

[Richard_Lawrence_Miller-4] Richard Lawrence Miller: The Encyclopedia of Addictive Drugs . Greenwood Publishing Group, 2002, ISBN 978-0-313-31807-8 , pp. 223 ( limited preview in Google Book search).