Metaraminol

Structural formula
General
Non-proprietary name	Metaraminol
other names	(1 R , 2 S ) -3 - [- 2-Amino-1-hydroxypropyl] phenol; (-) - α- (1-Aminoethyl) - m -hydroxybenzyl alcohol;
Molecular formula	C 9 H 13 NO 2 (metaraminol) ; C 13 H 19 NO 8 (metaraminol hydrogen tartrate ) ; C 9 H 13 NO 2 HCl (metaraminol hydrochloride ) ; C 9 H 13 NO 2 · C 2 H 2 O 4 · 2H 2 O (metaraminol · oxalate · Di hydrate ) ;
External identifiers / databases
PubChem	5906
DrugBank	DB00610
Wikidata	Q409981
Drug information
ATC code	C01 CA09
Drug class	Sympathomimetics
properties
Molar mass	167.21 g · mol -1 (metaraminol) ; 317.29 g · mol -1 (metaraminol bitartrate ·) ;
Melting point	176–177 ° C (metaraminol hydrogen tartrate) ; 190 ° C (metaraminol oxalate dihydrate) ;
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances danger
H and P phrases	H: 301-311-331
	P: 261-280-301 + 310-311
Toxicological data	440 mg kg −1 ( LD 50 , mouse , ip )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Metaraminol (trade names Aramine and Araminon ) is a drug from the group of sympathomimetics for the treatment of low blood pressure ( hypotension ).

Metaraminol is not approved for the treatment of permanent erections ( priapism ), but there have been case reports of its successful use. The active ingredient is also used to provoke suspected familial Mediterranean fever (FMF). The patient is given a single 10 mg dose; if an attack occurs within the next 48 hours, this is an indication of the presence of FMF.

Individual evidence

↑ ^a ^b ^c The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, p. 1024, ISBN 978-0-911910-00-1 .
↑ ^a ^b Data sheet Metaraminol (+) - bitartrate salt from Sigma-Aldrich , accessed on April 10, 2011 ( PDF ).
↑ McDonald M, Santucci R: Successful management of stuttering priapism using home self-injections of the alpha-agonist metaraminol. . In: Int Braz J Urol . 30, No. 2, 2004, pp. 121-2. doi : 10.1590 / S1677-55382004000200007 . PMID 15703094 .
↑ Koga S, Shiraishi K, Saito Y: Post-traumatic priapism treated with metaraminol bitartrate: case report. . In: The Journal of Trauma . 30, No. 12, 1990, pp. 1591-3. doi : 10.1097 / 00005373-199012000-00029 . PMID 2258979 .
^ Block T, Sturm W, Ernst G, Staehler G, Schmiedt E: [Metaraminol in therapy of various forms of priapism] . In: Urologist A . 27, No. 4, 1988, pp. 225-9. PMID 3140463 .
↑ Barakat MH, El-Khawad AO, Gumaa KA, El-Sobki NI, Fenech FF: Metaraminol provocative test: a specific diagnostic test for familial Mediterranean fever . In: Lancet . 1, No. 8378, 1984, pp. 656-7. PMID 6142351 .
^ Huppertz HI, Michels H: [The metaraminol provocation test in the diagnosis of familial Mediterranean fever] . In: Monthly Children's Health . 136, No. 5, 1988, pp. 243-5. PMID 3405225 .

[MerckIndex-1] The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, p. 1024, ISBN 978-0-911910-00-1 .

[Sigma-2] Data sheet Metaraminol (+) - bitartrate salt from Sigma-Aldrich , accessed on April 10, 2011 ( PDF ).

[McDonald-3] McDonald M, Santucci R: Successful management of stuttering priapism using home self-injections of the alpha-agonist metaraminol. . In: Int Braz J Urol . 30, No. 2, 2004, pp. 121-2. doi : 10.1590 / S1677-55382004000200007 . PMID 15703094 .

[Koga-4] Koga S, Shiraishi K, Saito Y: Post-traumatic priapism treated with metaraminol bitartrate: case report. . In: The Journal of Trauma . 30, No. 12, 1990, pp. 1591-3. doi : 10.1097 / 00005373-199012000-00029 . PMID 2258979 .

[Block-5] Block T, Sturm W, Ernst G, Staehler G, Schmiedt E: [Metaraminol in therapy of various forms of priapism] . In: Urologist A . 27, No. 4, 1988, pp. 225-9. PMID 3140463 .

[6] Barakat MH, El-Khawad AO, Gumaa KA, El-Sobki NI, Fenech FF: Metaraminol provocative test: a specific diagnostic test for familial Mediterranean fever . In: Lancet . 1, No. 8378, 1984, pp. 656-7. PMID 6142351 .

[7] Huppertz HI, Michels H: [The metaraminol provocation test in the diagnosis of familial Mediterranean fever] . In: Monthly Children's Health . 136, No. 5, 1988, pp. 243-5. PMID 3405225 .