CINNAMEDRINE

Details

Stereochemistry	UNKNOWN
Molecular Formula	C19H23NO
Molecular Weight	281.392
Optical Activity	UNSPECIFIED
Defined Stereocenters	0 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C(O)C1=CC=CC=C1)N(C)C\C=C\C2=CC=CC=C2

InChI

InChIKey=YMJMZFPZRVMNCH-FMIVXFBMSA-N

InChI=1S/C19H23NO/c1-16(19(21)18-13-7-4-8-14-18)20(2)15-9-12-17-10-5-3-6-11-17/h3-14,16,19,21H,15H2,1-2H3/b12-9+

HIDE SMILES / InChI

Molecular Formula	C19H23NO
Molecular Weight	281.392
Charge	0
Count

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	0 / 2
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3615570 | doi:10.1001/archinte.1982.00340210181040 Retrived from: http://jamanetwork.com/journals/jamainternalmedicine/article-abstract/602330

Cinnamedrine is an active ingredient of midol (a combination of cinnamedrine hydrochloride, aspirin, phenacetin, and caffeine) used to relieve dysmenorrhea. Midol was an over-the-counter drug, which was discontinued due to a marketing decision.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dysmenorrhea 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7103644	Primary		Not Provided 511	midol Approved Use Unknown

PubMed

Title	Date	PubMed
Antiarrhythmic-like actions of the smooth muscle spasmolytic agent, cinnamedrine, on action potentials of mammalian ventricular tissue.	1987	3615570
Cinnamedrine: potential for abuse.	1983-03	6887304

Patents

Sample Use Guides

In Vivo Use Guide

Midol (a combination of cinnamedrine hydrochloride, aspirin, phenacetin, and caffeine) - two tablets every four hours, with a maximum eight tablets per day.

Route of Administration: Oral

In Vitro Use Guide

It was examined influence of cinnamedrine on the smooth muscle relaxing properties using rat uterus. Cinnamedrine exhibited dose-related spasmolytic activity in the isolated spontaneously contracting rat uterus and in uterine tissue pretreated with oxytocin to augment spasms. The IC50's for cinnamedrine was 36.2 microM; the IC50's after oxytocin pretreatment was 25.7 microM for cinnamedrine.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:47:06 GMT 2025` Edited by `admin` on `Mon Mar 31 18:47:06 GMT 2025`
Record UNII	Y1245J8012
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CINNAMEDRINE

Official Name

English

CINNAMEDRINE [MART.]

Preferred Name

English

cinnamedrine [INN]

Common Name

English

CINNAMEDRINE [USAN]

Common Name

English

BENZENEMETHANOL, .ALPHA.-(1-(METHYL(3-PHENYL-2-PROPENYL)AMINO)ETHYL)-

Systematic Name

English

?-[1-(Cinnamylmethylamino)ethyl]benzyl alcohol

Systematic Name

English

Cinnamedrine [WHO-DD]

Common Name

English

CINNAMEDRINE [MI]

Common Name

English

CINNAMEDRINE [VANDF]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C87053