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 8583	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 8583	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 8583	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

Doses

Dose	Population	Adverse events
80 mg single, oral Recommended Dose: 80 mg Route: oral Route: single Dose: 80 mg Sources: https://pubmed.ncbi.nlm.nih.gov/27189530/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/27189530/	Other AEs: Anaphylaxis... Other AEs: Anaphylaxis Sources: https://pubmed.ncbi.nlm.nih.gov/27189530/
160 mg 3 times / day multiple, oral Studied dose Dose: 160 mg, 3 times / day Route: oral Route: multiple Dose: 160 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17439513/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17439513/	Other AEs: Abdominal pain, flatulenc... Other AEs: Abdominal pain flatulenc Constipation Sources: https://pubmed.ncbi.nlm.nih.gov/17439513/

AEs

AE	Dose	Population
Anaphylaxis	80 mg single, oral Recommended Dose: 80 mg Route: oral Route: single Dose: 80 mg Sources: https://pubmed.ncbi.nlm.nih.gov/27189530/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/27189530/
Abdominal pain	160 mg 3 times / day multiple, oral Studied dose Dose: 160 mg, 3 times / day Route: oral Route: multiple Dose: 160 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17439513/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17439513/
Constipation	160 mg 3 times / day multiple, oral Studied dose Dose: 160 mg, 3 times / day Route: oral Route: multiple Dose: 160 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17439513/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17439513/
flatulenc	160 mg 3 times / day multiple, oral Studied dose Dose: 160 mg, 3 times / day Route: oral Route: multiple Dose: 160 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17439513/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17439513/

PubMed

Title	Date	PubMed
(1E,4E)-1,5-Bis(2,4,6-trimeth-oxy-phen-yl)penta-1,4-dien-3-one.	2010-12-04	21522745
Synthesis and antitumor activity of diterpenylhydroquinone derivatives of natural ent-labdanes.	2010-09-17	20877240
(E)-1-(2-Fur-yl)-3-(2,4,6-trimeth-oxy-phen-yl)prop-2-en-1-one.	2010-09-15	21587546
A carbene-carbene complex equilibrium.	2010-08-11	20681697
Synthesis and biological evaluation of a novel series of 2,2-bisaminomethylated aurone analogues as anti-inflammatory and antimicrobial agents.	2010-07	20430485
Mesit-yl(2,4,6-trimeth-oxy-phen-yl)borinic acid.	2010-06-18	21587929
Solvation of dichlorocarbene: complexation with aryl ethers.	2010-01-14	19877654
6-(4-Bromo-phen-yl)-2-eth-oxy-4-(2,4,6-trimethoxy-phen-yl)nicotinonitrile.	2009-10-31	21578493
Ozonolysis of lignin models in aqueous solution: anisole, 1,2-dimethoxybenzene, 1,4-dimethoxybenzene, and 1,3,5-trimethoxybenzene.	2009-08-15	19746725
(E)-1-(4-Bromo-phen-yl)-3-(2,4,6-trimethoxy-phen-yl)prop-2-en-1-one.	2009-03-28	21582601
Development of a coupled diffusion denuder system combined with gas chromatography/mass spectrometry for the separation and quantification of molecular iodine and the activated iodine compounds iodine monochloride and hypoiodous acid in the marine atmosphere.	2009-03-01	19199811
Total synthesis of wasabidienones B1 and B0 via SIBX-mediated hydroxylative phenol dearomatization.	2008-11-20	18939801
A denuder-impinger system with in situ derivatization followed by gas chromatography-mass spectrometry for the determination of gaseous iodine-containing halogen species.	2008-11-14	18849042
C3 vanadium(V) amine triphenolate complexes: vanadium haloperoxidase structural and functional models.	2008-10-06	18774797
A xerogel-sequestered selenoxide catalyst for brominations with hydrogen peroxide and sodium bromide in an aqueous environment.	2008-09-05	18671430
Validation of a quantitative NMR method for suspected counterfeit products exemplified on determination of benzethonium chloride in grapefruit seed extracts.	2008-08-05	18456447
Leaf essential oil composition of three species of Myrcianthes from Monteverde, Costa Rica.	2008-07	18649320
Investigation of the dynamic stereochemistry of dimesityl-2,4,6-trimethoxyphenylmethane by complete lineshape analysis and 2D EXSY NMR spectroscopy.	2008-04	18273867
Sila-haloperidol, a silicon analogue of the dopamine (D2) receptor antagonist haloperidol: synthesis, pharmacological properties, and metabolic fate.	2008-01	18022977
Electron capture in charge-tagged peptides. Evidence for the role of excited electronic states.	2007-12	17951069
Transcriptomic and metabolite analyses of Cabernet Sauvignon grape berry development.	2007-11-22	18034876
Tissue-specific mRNA expression profiling in grape berry tissues.	2007-06-21	17584945
Bimolecular hole transfer from the trimethoxybenzene radical cation in the excited state.	2007-06-07	17480061
One-electron oxidation of alcohols by the 1,3,5-trimethoxybenzene radical cation in the excited state during two-color two-laser flash photolysis.	2007-03-15	17295459
Solvent-free iodination of organic molecules using the I(2)/urea-H(2)O(2) reagent system.	2007-02-21	17285178
The behavior of exciplex decay processes and interplay of radiationless transition and preliminary reorganization mechanisms of electron transfer in loose and tight pairs of reactants.	2007-01-18	17214455
Facile synthesis of 1,3,7-trihydroxyxanthone and its regioselective coupling reactions with prenal: simple and efficient access to osajaxanthone and nigrolineaxanthone F.	2006-06-23	16776532
Control of extremely fast competitive consecutive reactions using micromixing. Selective Friedel-Crafts aminoalkylation.	2005-08-24	16104743
Synthesis, characterization, and PGSE (1H and 19F) NMR diffusion studies on cationic (eta6- arene)Mn(CO)3+ complexes: boron counterion, ion pairing, and solvent dependences.	2005-08-08	16060650
Adsorption of single-ring organic compounds to wood charcoals prepared under different thermochemical conditions.	2005-06-01	15984774
The key role of phloroglucinol O-methyltransferase in the biosynthesis of Rosa chinensis volatile 1,3,5-trimethoxybenzene.	2004-05	15122041
Computational insight into the reaction intermediates in the glycosylation reaction assisted by donor heteroatoms.	2003-02-07	12558386
Two O-methyltransferases isolated from flower petals of Rosa chinensis var. spontanea involved in scent biosynthesis.	2003	16233496
Biosynthesis of the major scent components 3,5-dimethoxytoluene and 1,3,5-trimethoxybenzene by novel rose O-methyltransferases.	2002-07-17	12123815
Reactions of N-methyl-N-(4-biphenylyl)nitrenium ion with electron-rich arenes: laser flash photolysis and product studies.	2002-04-10	11929245
Metallocyclic receptors with Re(I)/Os(II)-based moieties: molecular photophysics and selective molecular sensing.	2001-06-01	11446645
Studies in polyphenol chemistry and bioactivity. 3.(1,2) stereocontrolled synthesis of epicatechin-4alpha,8-epicatechin, an unnatural isomer of the B-type procyanidins.	2001-02-23	11312959

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

PHLOROGLUCINOL TRIMETHYL ETHER

Preferred Name

English

TRIMETHYLPHLOROGLUCINOL

Systematic Name

English

Trimethylphloroglucinol [WHO-DD]

Common Name

English

1,3,5-TRIMETHOXYBENZENE [JAN]

Common Name

English

NSC-90060

Code

English

Code System Code Type Description

SMS_ID

100000092189