1,3,5-TRIMETHOXYBENZENE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H12O3
Molecular Weight	168.1898
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC(OC)=CC(OC)=C1

InChI

InChIKey=LKUDPHPHKOZXCD-UHFFFAOYSA-N

InChI=1S/C9H12O3/c1-10-7-4-8(11-2)6-9(5-7)12-3/h4-6H,1-3H3

HIDE SMILES / InChI

Description
Sources: http://www.has-sante.fr/portail/upload/docs/application/pdf/2012-11/spasfon_ct_9243.pdf
Curator's Comment: Description was created using several sources including: http://www.ema.europa.eu/docs/en_GB/document_library/contacts/ochassany_DI.pdf; https://www.ncbi.nlm.nih.gov/pubmed/14017697; https://www.ncbi.nlm.nih.gov/pubmed/15122041; https://www.ncbi.nlm.nih.gov/pubmed/17439513

1,3,5-trimethoxybenzene (trade name Spasfon (R), registered and marketed in France) is an antispasmodic drug acting on smooth muscle. It is indicated for symptomatic treatment of pain related to functional disorders of the gastrointestinal tract and biliary tract, urinary tract (renal colic) or gynecological pain, and to reduce early contractions during a pregnancy. It is widely prescribed in cases of intestinal disorders including infectious and other bowel disease, gastrointestinal symptoms, urinary tract and genital tract disease. Spasfon is produced as film-coated tablets and solution for injection. 1,3,5-Trimethoxybenzene is a key component of the Chinese rose odor. This compound is synthesized in three successive methylation steps from phloroglucinol, the initial precursor.

Originator

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Bowel function disorders 1 Sources: http://www.has-sante.fr/portail/upload/docs/application/pdf/2012-11/spasfon_ct_9243.pdf	Secondary	Approved 8429	SPASFON(R) Approved Use Indicated for symptomatic treatment of pain related to functional disorders of the gastrointestinal tract and biliary tract; treatment of spasm and acute pain of the urinary tract: renal colic; symptomatic treatment of painful spasm in gynaecology; adjuvant therapy for contractions during pregnancy, in combination with rest Launch Date 1973
Urinary tract disease and urinary tract stones 1 Sources: http://www.has-sante.fr/portail/upload/docs/application/pdf/2012-11/spasfon_ct_9243.pdf	Palliative	Approved 8429	SPASFON(R) Approved Use Indicated for symptomatic treatment of pain related to functional disorders of the gastrointestinal tract and biliary tract; treatment of spasm and acute pain of the urinary tract: renal colic; symptomatic treatment of painful spasm in gynaecology; adjuvant therapy for contractions during pregnancy, in combination with rest Launch Date 1973
Contractions during pregnancy 1 Sources: http://www.has-sante.fr/portail/upload/docs/application/pdf/2012-11/spasfon_ct_9243.pdf	Palliative	Approved 8429	SPASFON(R) Approved Use Indicated for symptomatic treatment of pain related to functional disorders of the gastrointestinal tract and biliary tract; treatment of spasm and acute pain of the urinary tract: renal colic; symptomatic treatment of painful spasm in gynaecology; adjuvant therapy for contractions during pregnancy, in combination with rest Launch Date 1973

PubMed

Title	Date	PubMed
Metallocyclic receptors with Re(I)/Os(II)-based moieties: molecular photophysics and selective molecular sensing.	2001 Jun 1	11446645
Reactions of N-methyl-N-(4-biphenylyl)nitrenium ion with electron-rich arenes: laser flash photolysis and product studies.	2002 Apr 10	11929245
Biosynthesis of the major scent components 3,5-dimethoxytoluene and 1,3,5-trimethoxybenzene by novel rose O-methyltransferases.	2002 Jul 17	12123815
Computational insight into the reaction intermediates in the glycosylation reaction assisted by donor heteroatoms.	2003 Feb 7	12558386
Control of extremely fast competitive consecutive reactions using micromixing. Selective Friedel-Crafts aminoalkylation.	2005 Aug 24	16104743
Adsorption of single-ring organic compounds to wood charcoals prepared under different thermochemical conditions.	2005 Jun 1	15984774
Electron capture in charge-tagged peptides. Evidence for the role of excited electronic states.	2007 Dec	17951069
Solvent-free iodination of organic molecules using the I(2)/urea-H(2)O(2) reagent system.	2007 Feb 21	17285178
Bimolecular hole transfer from the trimethoxybenzene radical cation in the excited state.	2007 Jun 7	17480061
Transcriptomic and metabolite analyses of Cabernet Sauvignon grape berry development.	2007 Nov 22	18034876
Investigation of the dynamic stereochemistry of dimesityl-2,4,6-trimethoxyphenylmethane by complete lineshape analysis and 2D EXSY NMR spectroscopy.	2008 Apr	18273867
Validation of a quantitative NMR method for suspected counterfeit products exemplified on determination of benzethonium chloride in grapefruit seed extracts.	2008 Aug 5	18456447
Sila-haloperidol, a silicon analogue of the dopamine (D2) receptor antagonist haloperidol: synthesis, pharmacological properties, and metabolic fate.	2008 Jan	18022977
A carbene-carbene complex equilibrium.	2010 Aug 11	20681697
Mesit-yl(2,4,6-trimeth-oxy-phen-yl)borinic acid.	2010 Jun 18	21587929
(E)-1-(2-Fur-yl)-3-(2,4,6-trimeth-oxy-phen-yl)prop-2-en-1-one.	2010 Sep 15	21587546

Patents

Sample Use Guides

In Vivo Use Guide

6 tablets per 24 hours

Route of Administration: Oral

In Vitro Use Guide

Assays for halogenation by neutrophils and eosinophils from the blood of normal volunteers and patients with eosinophilia were carried out using labeled with radioactive carbon 1,3,5-trimethoxybenzene at 1 X 10(-4) M (14C = 0.5 nCi/ml). Total amount of active halogen trapped by 1,3,5-trimethoxybenzene from eosinophils increases by over 2-fold as the added bromide concentration increases from 0 to 100 microM, with approximately 40 nmol of halogen trapped per million cells at the highest bromide level.

Name

Type

Language

1,3,5-TRIMETHOXYBENZENE

Systematic Name

English

TRIMETHYLPHLOROGLUCINOL

Systematic Name

English

Trimethylphloroglucinol [WHO-DD]

Common Name

English

PHLOROGLUCINOL TRIMETHYL ETHER [INCI]

Common Name

English

PHLOROGLUCINOL TRIMETHYL ETHER

Official Name

English

1,3,5-TRIMETHOXYBENZENE [JAN]

Common Name

English

NSC-90060

Code

English

Code System Code Type Description

SMS_ID

100000092189