Pentazocine

Structural formula
	1: 1 mixture of (all- R ) -form (left) and (all- S ) -form (right)
General
Non-proprietary name	Pentazocine
other names	(1 RS , 9 RS , 13 RS ) -1,13-dimethyl-10- (3-methyl-2-buten-1-yl) -10-azatricyclo [7.3.1.0 2.7 ] trideca-2,4, 6-trien-4-ol ( IUPAC ) ; (2 RS , 6 RS , 11 RS ) -2'-Hydroxy-5,9-dimethyl-2- (3,3-dimethylallyl) -6,7-benzomorphane; Pentazocinum ( Latin ) ;
Molecular formula	C 19 H 27 NO; C 19 H 27 NO · HCl ( hydrochloride ) ;
Brief description	white to almost white powder
External identifiers / databases
EC number	206-634-6
ECHA InfoCard	100.006.032
PubChem	441278
ChemSpider	390041
DrugBank	DB00652
Wikidata	Q415793
Drug information
ATC code	N02 AD01
Drug class	Opioid - analgesics
properties
Molar mass	285.42 g · mol -1 ; 321.88 g · mol -1 (hydrochloride) ; 375.50 g · mol -1 (lactate) ;
Physical state	firmly
Melting point	145.4-147.2 ° C
pK s value	8.88
solubility	very bad in water (30 mg l −1 at 25 ° C)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	305 mg kg −1 ( LD 50 , mouse , oral ) ; 139–211 mg kg −1 ( LD 50 , rat , sc ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Pentazocine is a highly effective pain reliever, synthetic drug from the group of opioid analgesics ( WHO level 3). It is subject to narcotics law, but has practically not been used in Germany (sold as Fortral ) since 2006.

effect

Pentazocine binds to opioid receptors , both as an agonist and an antagonist ; the mechanism of action is similar to that of nalbuphin . Because of this partially antagonistic effect, the substance can trigger a withdrawal syndrome in opiate addicts. The potency corresponds to about 1/6 to 1/3 of that of morphine , the half-life or analgesic duration of action is two to three hours. The peroral bioavailability is only around 20% due to the strong first-pass effect .

Pentazocine include functions such as selective agonist of κ opioid - receptor . Like other substances with κ-opioid agonistic effects (e.g. salvinorin A ), pentazocine therefore (in higher doses) shows psychoactive / hallucinogenic effects.

Side effects

Pentazocine increases blood pressure and heart rate . Side effects are sedation , increased tone of the smooth muscles of the gastrointestinal tract with a tendency to constipation , muscle cramps, spasm of the urinary bladder , visual disturbances, loss of appetite, changes in taste and decreased sex drive.

Other Information

Pentazocine was patented by Sterling Drug in 1962. Finished medicinal products containing pentazocine ( Fortral ) have not been on the market in Germany since 2006, due to the expiry of the fictitious approval . Fortral was launched on the German market in 1968. Even in Austria, Switzerland ( Fortalgesic ) and several other European countries, finished medicinal products containing pentazocin are no longer approved.

Pentazocine is on the Anti-Doping Agency's Prohibited List.

Pentazocine is chiral , used medicinally (as tablets, capsules, suppositories or injection solution) is the racemate . The lactate (lactic acid salt ) and the hydrochloride of pentazocine are pharmaceutically relevant .

Individual evidence

↑ European Pharmacopoeia Commission (ed.): European Pharmacopoeia. 5th edition . tape 5.0-5.8 , 2006.
^ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; P. 1229, ISBN 978-0-911910-00-1 .
↑ ^a ^b Entry on pentazocine in the ChemIDplus database of the United States National Library of Medicine (NLM) .
^ Entry on pentazocine in the DrugBank of the University of Alberta .
↑ ^a ^b data sheet (-) - Pentazocine from Sigma-Aldrich , accessed on April 18, 2011 ( PDF ).
^ ^A ^b Römpp Chemie Lexikon, 10th edition, 1998, Georg Thieme Verlag, Stuttgart - New York.
↑ Eberhard Klaschik : Pain therapy and symptom control in palliative medicine. In: Stein Husebø , Eberhard Klaschik (ed.): Palliative medicine. 5th edition, Springer, Heidelberg 2009, ISBN 3-642-01548-4 , pp. 207-313, here: p. 233.
^ Mutschler, Geisslinger, Kroemer, Schäfer-Korting, Mutschler drug effects, 9th edition, 2008, ISBN 3-8047-1952-X .
^ Prohibited list ( memento from July 19, 2014 in the Internet Archive ) of the World Anti-Doping Agency (WADA) (PDF, English; 177 kB).

[1] European Pharmacopoeia Commission (ed.): European Pharmacopoeia. 5th edition . tape 5.0-5.8 , 2006.

[MERCK_Index-2] The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; P. 1229, ISBN 978-0-911910-00-1 .

[ChemIDplus-3] Entry on pentazocine in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[4] Entry on pentazocine in the DrugBank of the University of Alberta .

[sigma-5] ta sheet (-) - Pentazocine from Sigma-Aldrich , accessed on April 18, 2011 ( PDF ).

[Römpp_Chemie_Lexikon_1998-6] A ^b Römpp Chemie Lexikon, 10th edition, 1998, Georg Thieme Verlag, Stuttgart - New York.

[7] Eberhard Klaschik : Pain therapy and symptom control in palliative medicine. In: Stein Husebø , Eberhard Klaschik (ed.): Palliative medicine. 5th edition, Springer, Heidelberg 2009, ISBN 3-642-01548-4 , pp. 207-313, here: p. 233.

[MAW9-8] Mutschler, Geisslinger, Kroemer, Schäfer-Korting, Mutschler drug effects, 9th edition, 2008, ISBN 3-8047-1952-X .

[9] Prohibited list ( memento from July 19, 2014 in the Internet Archive ) of the World Anti-Doping Agency (WADA) (PDF, English; 177 kB).