racephedrine

{{Short description|Pharmaceutical drug}}

{{Infobox drug

| drug_name =

| image = Ephedrine enantiomers.svg

| width = 200px

| caption = (−)-(1R,2S)-ephedrine (top),
(+)-(1S,2R)-ephedrine (bottom)

| pronounce =

| tradename = Efetonina; Ephoxamine

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| class = Norepinephrine releasing agent; Sympathomimetic; Bronchodilator; Psychostimulant

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| CAS_number = 90-81-3

| CAS_supplemental =

| PubChem = 5032

| IUPHAR_ligand =

| DrugBank = DB14752

| ChemSpiderID = 4856

| UNII = 03VRY66076

| KEGG = C22822

| ChEBI =

| ChEMBL = 279157

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| synonyms = Racemic ephedrine; (±)-Ephedrine; dl-Ephedrine; (1RS,2SR)-Ephedrine

| IUPAC_name = 2-(methylamino)-1-phenylpropan-1-ol

| C=10 | H=15 | N=1 | O=1

| SMILES = CC(C(C1=CC=CC=C1)O)NC

| StdInChI = 1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3

| StdInChIKey = KWGRBVOPPLSCSI-UHFFFAOYSA-N

}}

Racephedrine, also known as racemic ephedrine and sold under the brand names Efetonina and Ephoxamine among others, is the racemic form of ephedrine which has been used as a bronchodilator to treat asthma.{{cite book | author=Schweizerischer Apotheker-Verein | title=Index Nominum 2000: International Drug Directory | publisher=Medpharm Scientific Publishers | year=2000 | isbn=978-3-88763-075-1 | url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA390 | access-date=30 August 2024 | page=390}}{{cite web | title=Racephedrine: Uses, Interactions, Mechanism of Action | website=DrugBank Online | date=31 December 1995 | url=https://go.drugbank.com/drugs/DB14752 | access-date=30 August 2024}}{{cite web | title=Racephedrine | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/5032 | access-date=30 August 2024}}{{cite journal | vauthors = Tapay NJ | title = A racephedrine-phenyltoloxamine-containing compound (Ephoxamine) in the treatment of bronchial asthma | journal = Curr Ther Res Clin Exp | volume = 3 | issue = | pages = 305–312 | date = July 1961 | pmid = 13775237 | doi = | url = }}{{cite journal | vauthors = Dubois de Montreynaud JM, Kochman S, Charreire J, Fondeville D, Houlon JP, Doco | title = [Delayed-action effect of a racephedrine, theophylline and phenobarbital combination on asthma. Study on 100 cases] | language = French | journal = Therapie | volume = 23 | issue = 4 | pages = 987–994 | date = 1968 | pmid = 5744603 | doi = | url = }} More specifically, it is a racemic mixture of (1R,2S)- and (1S,2R)-enantiomers. Conversely, ephedrine is the enantiopure (1R,2S)-enantiomer. Racephedrine has been marketed for medical use in Italy. Like ephedrine, racephedrine is a releasing agent of norepinephrine and to a much lesser extent of dopamine. Both ephedrine enantiomers are active in this regard, but ephedrine ((1R,2S)-ephedrine) has greater potency than (1S,2R)-ephedrine.

class="wikitable sortable" style="font-size:small;" |+ Monoamine release by ephedrine and related agents ({{Abbrlink|EC50|half maximal effective concentration}}, nM){{cite journal | vauthors = Rothman RB, Baumann MH | title = Monoamine transporters and psychostimulant drugs | journal = Eur. J. Pharmacol. | volume = 479 | issue = 1–3 | pages = 23–40 | year = 2003 | pmid = 14612135 | doi = 10.1016/j.ejphar.2003.08.054}}{{cite journal | vauthors = Rothman RB, Baumann MH | title = Therapeutic potential of monoamine transporter substrates | journal = Curr Top Med Chem | volume = 6 | issue = 17 | pages = 1845–1859 | date = 2006 | pmid = 17017961 | doi = 10.2174/156802606778249766 | url = }}
Compound	data-sort-type="number" | {{abbrlink|NE|Norepinephrine}}	data-sort-type="number" | {{abbrlink|DA|Dopamine}}	data-sort-type="number" | {{abbrlink|5-HT|Serotonin}}	Ref
Dextroamphetamine (S(+)-amphetamine)	6.6–7.2	5.8–24.8	698–1765	{{cite journal | vauthors = Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, Partilla JS | title = Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin | journal = Synapse | volume = 39 | issue = 1 | pages = 32–41 | date = January 2001 | pmid = 11071707 | doi = 10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3 | url = }}{{cite journal | vauthors = Baumann MH, Partilla JS, Lehner KR, Thorndike EB, Hoffman AF, Holy M, Rothman RB, Goldberg SR, Lupica CR, Sitte HH, Brandt SD, Tella SR, Cozzi NV, Schindler CW | title = Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products | journal = Neuropsychopharmacology | volume = 38 | issue = 4 | pages = 552–562 | year = 2013 | pmid = 23072836 | pmc = 3572453 | doi = 10.1038/npp.2012.204 }}
S(–)-Cathinone	12.4	18.5	2366	{{cite journal | vauthors = Rothman RB, Vu N, Partilla JS, Roth BL, Hufeisen SJ, Compton-Toth BA, Birkes J, Young R, Glennon RA | title = In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates | journal = J Pharmacol Exp Ther | volume = 307 | issue = 1 | pages = 138–145 | date = October 2003 | pmid = 12954796 | doi = 10.1124/jpet.103.053975 | url = }}
Ephedrine ((–)-ephedrine; (1R,2S)-ephedrine)	43.1–72.4	236–1350	>10000
(+)-Ephedrine ((1S,2R)-ephedrine)	218	2104	>10000
Dextromethamphetamine (S(+)-methamphetamine)	12.3–13.8	8.5–24.5	736–1291.7	{{cite journal | vauthors = Baumann MH, Ayestas MA, Partilla JS, Sink JR, Shulgin AT, Daley PF, Brandt SD, Rothman RB, Ruoho AE, Cozzi NV | title = The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue | journal = Neuropsychopharmacology | volume = 37 | issue = 5 | pages = 1192–203 | date = April 2012 | pmid = 22169943 | pmc = 3306880 | doi = 10.1038/npp.2011.304 | url = }}
Levomethamphetamine (R(–)-methamphetamine)	28.5	416	4640
(+)-Phenylpropanolamine ((+)-norephedrine)	42.1	302	>10000
(–)-Phenylpropanolamine ((–)-norephedrine)	137	1371	>10000
Cathine ((+)-norpseudoephedrine)	15.0	68.3	>10000
(–)-Norpseudoephedrine	30.1	294	>10000
(–)-Pseudoephedrine	4092	9125	>10000
Pseudoephedrine ((+)-pseudoephedrine)	224	1988	>10000
colspan="7" style="width: 1px; background-color:#eaecf0; text-align: center;" | The smaller the value, the more strongly the substance releases the neurotransmitter. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds.

Racephedrine has been used in a variety of combination drugs with other agents, including theophylline, aminophylline, oxtriphylline, phenobarbital, pentobarbital, pyrilamine, phenacetin, salicylamide, ascorbic acid, and opium, among others.{{cite book | title=Project Label: Alphabetical Listing by Drug Product | publisher=Department of Justice, Drug Enforcement Administration, Office of Compliance and Regulatory Affairs, Regulatory Support Division, Information Systems Section | year=1979 | url=https://books.google.com/books?id=8HJc_WTwdNsC&pg=PT235 | access-date=2024-08-31 | page=235}} Brand names of these combination preparations have included Amiphedrin, Amodrine, Amodrine E C, Asphamal-D, Asthmadrin, Cenamal, Cholarace, Phedrahist, Respirol, Salidin, Synate-M, and Synophedal.