Compound: guaifenesin
SMILES: O(c1c(OC)cccc1)CC(O)CO
InChIKey: HSRJKNPTNIJEKV-UHFFFAOYSA-N
Synonyms: guaifenesin, 93-14-1, Guaiphenesin, Guaiacol glyceryl ether, 3-(2-methoxyphenoxy)propane-1,2-diol, GLYCERYL GUAIACOLATE, Glycerol guaiacolate, Guaiphenesine, Methphenoxydiol, Aeronesin, Calmipan, Guaiamar, Guaianesin, Hustosil, Myocaine, Robitussin, Aresol, Mucinex, Dilyn, Resyl, Guaiacuran, Guaiacurane, Guajacuran, Guayanesin, Reorganin, Myoscain, Neuroton, Respenyl, Creson, Oresol, Oreson, Glycerin guaiacolate, 3-(o-Methoxyphenoxy)-1,2-propanediol, Guaiacol glycerol ether, Relaxil G, Guaifenesine, Glycotuss, Miocaina, Ritussin, Glyceryl guaiacyl ether, o-Methoxyphenyl glyceryl ether, Guaifenesinum, Glycerylguaiacol, 1,2-Propanediol, 3-(2-methoxyphenoxy)-, Guaifenesina, MY 301, Guaifensin, SL-90, alpha-Glyceryl guaiacol ether, 1,2-Dihydroxy-3-(2-methoxyphenoxy)propane, alpha-Glyceryl guaiacolate ether, 1,2-Propanediol, 3-(o-methoxyphenoxy)-, Glycerol alpha-guaiacyl ether, DTXSID5023114, Glycerol alpha-(o-methoxyphenyl)ether, NSC-62112, Glycerol alpha-(2-methoxyphenyl) ether, CVT-2534, NSC62112, 495W7451VQ, CHEBI:5551, DTXCID403114, OBREDON COMPONENT GUAIFENESIN, FLOWTUSS COMPONENT GUAIFENESIN, Guaiphenezine, Humibid, ScottTussin, Scott Tussin, Guaiacolate, Glycerol, Ether, Guaiacol Glyceryl, Glyceryl Ether, Guaiacol, robafen, Guiafenesin, Guifenesin, Amonidron, Broncomar, Gecolate, Guailaxin, Liqufruta, Pharbinex, Mucosa, topcare tussin, Tusnel, Famel, Franolyn chesty, Guaap, Mucus, Akin, My301, Revasol Tussin, Sunmark Tussin, Walgreen Cherry, Broncomar Sf, Gadavyt Cough, Mucus Relief, Siltussin Sa, Tussin Chest, Chest Congestion, Geri-Tussin, Muca Clear, Rompe Pecho, Air Power, Cough Out, DRx Choice, Mucosa Guifenesin, Reeses TABtussin, good sense tussin, Mucus Relief ER, Rompe Pecho Sf, Tusnel EX, Mucus Relief Max, CurNEX, CVS Adult Mucus, Rompe Pecho EX, Simpex Guaifenesin, Tussin Expectorant, welby mucus relief, CuraTUSSIN, Topcare Mucus ER, Leader Cough Tabs, Marcs Mucus Relief, Organ-I Nr, Reliable-1 Tussin, Topco Mucus Relief, Kids-EEZE, TopCare Tab Tussin, basic care mucus er, Curist Mucus Relief, Equate Mucus Relief, Guaifenesin 200mg, Guaifenesin 400mg, Kroger Mucus Relief, Leader Mucus Relief, Palatos Expectorante, Ritussin Expectorant, Safrel Mucus Relief, Tixylix chesty cough, Broncomar Expectorant, caring mill mucus er, Guaifenesin Injection, EXCAUGH, MUCUSOL, Sunmark Mucus Relief, Dg Health Mucus ER, Good Sense Mucus ER, Guaifenesin 200 mg, Guaifenesin 400 mg, Guaifenesin 600 mg, Robafen Cough Formula, Childrens Mucus Relief, Mucus Extended Release, Refenesen Mucus Relief, Giltuss EX Expectorant, Selecthealth Tussin DM, Chest Congestion Relief, dg health mucus er max, Geri-tussin Expectorant, Guaifenesin 1200 mg, Kids-eeze Chest Relief, RefChem:5872, Rugby Cough Guaifenesin, 12 Hour Mucus Relief, GUAIFENESIN-ODAAT, Mucus Relief 600 mg, basic care mucus er max, DRx Choice Fruit Punch, SDA Laboratories Tussin, Meijer Adult Mucus Plus, MMM guaifenesin solution, Mucinex Maximum Strength, Select Brand Tab Tussin, Broncomar Expectorant SF, Up and Up Mucus Relief, Guaifenesin 100mg/5mL, QCH Adult Tussin 541, Select Brand Mucus Relief, Diabetic Tussin Expectorant, Good Neighbor Adult Tussin, Guaifensin Extended-Release, Betr chest congestion relief, Guaifenesin Extended Release, Guaifenesin Extended-Release, Quality Choice Mucus Relief, Gecolate, Glycodex Injection, Select Brand Coughtab 400, Maximum Strength Mucus Relief, Mucus Relief Chest Congestion, Mucus Relief Extended Release, Mucus Relief Extended-Release, Mucus Relief Maximum Strength, Rugby Chest Congestion Relief, Leader Chest Congestion Relief, Meijer Chest Congestion Relief, Mucus Relief Immediate Release, Shopko Chest Congestion Relief, Foster and Thrive Mucus Relief, TopCare Chest Congestion Relief, Berkley and Jensen Mucus Relief, Equaline Chest Congestion Relief, Good Neighbor Pharmacy Tabtussin, rugby mucus and chest congestion, Childrens Giltuss EX Expectorant, Good Neighbor Pharmacy Mucus ER, Scot-tussin Expectorant Sf Cough, Childrens Chest Congestion Relief, CVS Adult Mucus chest congestion, R05CA03, Refenesen Chest Congestion Relief, GUAIFENESIN 400MG CAPLETS, ROBITUSSIN CHEST CONGESTION, Childrens Mucinex Chest Congestion, Healthmart Chest Congestion Relief, Robitussin Direct Chest Congestion, Always Save Chest Congestion Relief, Good Neighbor Pharmacy Mucus Relief, GUAIFENESIN-ODAAT 1200 MG, CVS HEALTH Chest Congestion Relief, Tussin Guifenesin Expectrorant Syrup, Betr remedies chest congestion relief, Curist Mucus Relief Maximum Strength, Guaifenesin Extended Release 600 mg, Guaifenesin Extended-Release 600 mg, Nirolex for chesty cough decongestant, Rugby Chest Congestion Relief G450, Leader Chest Congestion Relief G450, Premier Value Chest Congestion Relief, CVS Adult Mucus plus Chest Congestion, Guaifenesin Extended Release 1200 mg, Guaifenesin Extended-Release 1200 mg, MAX Tussin Mucus and Chest Congestion, Preferred Plus Chest Congestion Relief, Robitussin Mucus Plus Chest Congestion, Rugby Mucus and Chest Congestion 541, Childrens Chest Congestion Relief Grape, Childrens Mucus Relief Chest Congestion, Family Wellness Chest Congestion Relief, Mucus Relief Maximum Strength 1200 mg, Tussin Adult Mucus and Chest Congestion, Meijer Adult Mucus Plus chest congestion, Always Save Chest Congestion Relief GUAF, DG Health Immediate Release Mucus Relief, Foster and Thrive Chest Congestion Relief, Akin Expectorant Formula Strawberry Banana, Equaline Tussin Mucus and Chest Congestion, The Medicine Shoppe Chest Congestion Relief, Tussin Mucus and Chest Congestion Sugar Free, (2RS)-3-(2-Methoxyphenoxy)propane-1,2-diol, EXPECTORANT GUAIFENESIN EXTENDED-RELEASE, Mucus Relief Extended Release Maximum Strength, MAX Tussin Mucus and Chest Congestion Sugar Free, Crcle Guaifenesin Extended-Release Tablets, 600 mg, Crcle Guaifensin Extended Release Tablet, 1200 mg, Leader Adult Tussin Mucus and Chest Congestion 541, Good Neighbor Adult Tussin Mucus and chest congestion, Mucinex Fast-Max Chest Congestion Honey and Berry Flavor, MUCUS RELIEF GUAIFENESIN EXTENDED-RELEASE 1200 mg, MUCUS RELIEF GUAIFENESIN EXTENDED-RELEASE 600 mg, Little Remedies Little Colds Mucus Relief Expectorant Melt Aways, 202-222-5, Breonesin, Bronchol, Propanosedyl, Cortussin, Dorassin, Flartussin, Guaiphesin, Myoscaine, Tenntuss, Gaiamar, Hytuss, Myocain, Reduton, Sirotol, Tulyn, Glyceryl guaiacol, Methoxypropanediol, Metossipropandiolo, Metfenossidiolo, Amonidrin, Guajamar, Guiaphenesin, Hustodil, Mintosyl, Miocurin, Miorelax, Mucostop, Muskurelax, Myorelax, Neurotone, Glyceryl guaicolate, Glyceryl guiacolate, Guanar, Respil, Gvaja, Resil, Tolyn, Tulyl, 3-(2-Methoxyphenoxy)-1,2-propanediol, Guaiacolglicerinetere, Guaia-rom, Relaxyl-G, Guaicol glyceryl ether, Gnaifenesin, Guaiacyl glyceryl ether, Guaicol glycerine ether, Organidin NR, Glycero-guaiacol ether, Guaiacol glycerin ether, Amonidren, Pneumomist, Trecid, rac Guaifenesin, Glycerin monoguaiacol ether, Guajacol-glycerinaether, Glyceryl guaiacol ether, 3-o-Methoxyphenoxypropane 1:2-diol, Glyceryl guaiacolate ether, Glycerol mono(2-methoxyphenyl) ether, XL-90, Actifed C, Guaiacolic acid, ester with glycerol, G 87, Glycerol-alpha-guajakolether, MFCD00016873, component of Quibron, 3-(o-Methoxyphenoxy)-propanediol-1,2, component of Hycotuss, Glycerol .alpha.-guiacyl ether, .alpha.-Glyceryl guaiacol ether, Glycerol .alpha.-guaiacyl ether, Guajacol-.alpha.-glycerin-ether, component of Brondecon, .alpha.-Glyceryl guaiacolate ether, Glycerol .alpha.-monoguaiacol ether, component of Quibron Plus, 1,2,3-Propanetriol, ether with 2-methoxyphenol, Glycerol .alpha.-(o-methoxyphenyl)ether, Glycerol .alpha.-(2-methoxyphenyl) ether, component of Colrex Expectorant, 2-G, 2/G, Equicol, Glycodex, Colrex expectorant, MY-301, Tenntus, Tussin, Glycerinmonoguaiacol ether, Benylin-E, Lufyllin-GG, Aether glycerinoguaiacolicus, Guaifenesine [INN-French], Guaifenesinum [INN-Latin], Guajacol-alpha-glycerinether, Tedral Expectorant, (component of) Deconsal II, Glycerol alpha-guiacyl ether, Guaifenesina [INN-Spanish], Glycerol alpha-monoguaiacol ether, Glycerol-alpha-monoguaiacol ether, Guajacol-glycerinaether [German], HSDB 3089, SR-01000737186, Glycerol mono(2-methoxyphenyl)ether, EINECS 202-222-5, Glycerol-alpha-guajakolether [Czech], NSC 62112, Glycerol alpha-(o-methoxyphenyl) ether, BRN 2049375, glycerin ether, Glyc, AI3-24947, Guaifenesin CRS, UNII-495W7451VQ, Q-Tussin, CAS-93-14-1, NCGC00016350-01, Hustosil (TN), Prestwick_231, Entex (Salt/Mix), HUMABID, Dimacol (Salt/Mix), Kwelcof (Salt/Mix), Hycotuss (Salt/Mix), Guaifenesin [USAN:USP:INN:BAN:JAN], Brondecon (Salt/Mix), Congestac (Salt/Mix), Triaminic (Salt/Mix), Dilor G (Salt/Mix), Guaifenesin (Standard), Spectrum_000835, Pneumomist (Salt/Mix), Q-Tussin (Salt/Mix), Glycerol-a-guajakolether, 3-(2-Methoxy-phenoxy)-propane-1,2-diol, Mucinex D (Salt/Mix), ROBITUSSIN (TN), Glycerol a-guiacyl ether, Tussar-2 (Salt/Mix), Brexin EX (Salt/Mix), Tussar SF (Salt/Mix), GUAIFENESIN [MI], Guaifenesin(Guaiphenesin), a-Glyceryl guaiacol ether, Glycerol a-guaiacyl ether, Mucinex DM (Salt/Mix), Prestwick0_000776, Prestwick1_000776, Prestwick2_000776, Prestwick3_000776, Spectrum2_001104, Spectrum3_000444, Spectrum4_000566, Spectrum5_000758, GlyTouCan:G20562UD, GUAIFENESIN [INN], GUAIFENESIN [JAN], Lufyllin-GG (Salt/Mix), Naldecon-EX (Salt/Mix), (+-)-3-(o-Methoxyphenoxy)-1,2-propanediol, Guaifenesin (Guaiphenesin), GUAIFENESIN [HSDB], GUAIFENESIN [USAN], CHEMBL980, Theolair Plus (Salt/Mix), GUAIFENESIN [VANDF], Robitussin CF (Salt/Mix), SCHEMBL4321, a-Glyceryl guaiacolate ether, Neothylline-GG (Salt/Mix), GUAIFENESIN [MART.], Oprea1_193170, Pneumotussin HC (Salt/Mix), WLN: Q1YQ1OR BO1, 1, 3-(o-methoxyphenoxy)-, Bronkaid Caplets (Salt/Mix), BSPBio_000852, BSPBio_002088, Glycerol a-monoguaiacol ether, GUAIFENESIN [USP-RS], GUAIFENESIN [WHO-DD], KBioGR_000972, KBioSS_001315, Slo-Phyllin GG (Salt/Mix), 1,2-Propanediol, 3-(2-methoxyphenoxy)- (+-)-, 4-06-00-05576 (Beilstein Handbook Reference), MLS000028402, 1, 3-(2-methoxyphenoxy)-, DivK1c_000248, SPECTRUM1500321, Glycerol-.alpha.-guajakolether, SPBio_001208, SPBio_002791, PV Tussin Tablet (Salt/Mix), Tedral Expectorant (Salt/Mix), BPBio1_000938, GTPL7617, orb1310335, Guaifenesin (JP18/USP/INN), GUAIFENESIN [GREEN BOOK], SCHEMBL29759010, Tussi-Organidin NR (Salt/Mix), HMS500M10, HY-B0264R, KBio1_000248, KBio2_001315, KBio2_003883, KBio2_006451, KBio3_001308, Contac Cough Formula (Salt/Mix), GUAIFENESIN [ORANGE BOOK], MSK2561, Ranolazine metabolite CVT-2534, Ru-Tuss DE Tablets (Salt/Mix), Glycerol a-(o-methoxyphenyl)ether, NINDS_000248, GUAIFENESIN [EP MONOGRAPH], HMS1570K14, HMS1920B15, HMS2090K20, HMS2091H21, HMS2097K14, HMS2231M20, HMS3369E03, HMS3369N15, HMS3651I17, HMS3714K14, HMS5079P20, Isoclor Expectorant C (Salt/Mix), Pharmakon1600-01500321, Polaramine Expectorant (Salt/Mix), GUAIFENESIN [USP MONOGRAPH], G20562UD, Glycerol a-(2-methoxyphenyl) ether, HY-B0264, LCA24875, Tox21_110389, Tox21_302094, BBL009981, CCG-39687, EBC-11064, NSC757052, s1740, STK365152, Glycerol, 1-(2-methoxyphenyl) ether, AKOS005435152, MUCINEX D COMPONENT GUAIFENESIN, Tox21_110389_1, DB00874, FG61559, KS-5306, MUCINEX DM COMPONENT GUAIFENESIN, NSC-757052, Guaiacol glyceryl ether, >=98% (GC), IDI1_000248, 3-(2-Methoxyphenoxy)-1, 2-propanediol, NCGC00094689-01, NCGC00094689-02, NCGC00094689-03, NCGC00094689-04, NCGC00094689-06, NCGC00255343-01, AC-26819, DA-73936, SMR000058387, SY001753, SBI-0051397.P003, AB00052006, G0159, NS00007812, ST50330628, SW196538-3, T0739, 1,3-Propanetriol, ether with 2-methoxyphenol, D00337, D70850, 3-{[2-(methyloxy)phenyl]oxy}propane-1,2-diol, AB00052006-10, AB00052006-11, AB00052006_12, AB00052006_13, Guaifenesin; Ranolazine Hydrochloride Impurity F, EN300-25998675, F787582, Q420682, SR-01000737186-2, SR-01000737186-3, (+/-)-3-(O-METHOXYPHENOXY)-1,2-PROPANEDIOL, BRD-A90515964-001-05-8, BRD-A90515964-001-09-0, BRD-A90515964-001-15-7, BRD-A90515964-001-16-5, Z1255415511, 1,2-PROPANEDIOL, 3-(2-METHOXYPHENOXY)- (+/-)-, Guaifenesin, European Pharmacopoeia (EP) Reference Standard, Guaifenesin, United States Pharmacopeia (USP) Reference Standard, Guaifenesin, Pharmaceutical Secondary Standard; Certified Reference Material, 3-(o-Methoxyphenoxy)-1,2-propanediol, guaiacol gly  ceryl ether, robitussin, Guaifenesin for peak identification, European Pharmacopoeia (EP) Reference Standard, InChI=1/C10H14O4/c1-13-9-4-2-3-5-10(9)14-7-8(12)6-11/h2-5,8,11-12H,6-7H2,1H
Theoretical properties:
molecular_formula: C10H14O4
molecular_weight: 198.22 g/mol
exact_mass: 198.08920892 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 5
heavy_atom_count: 14
topological_polar_surface_area: 58.9 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Minute rhombic prisms from ether
color: Minute rhombic prisms from ether
odor: SLIGHT CHARACTERISTIC ODOR
melting_point: 78.5-79
Descriptions:
pubchem: Guaifenesin is a member of methoxybenzenes.
chembl: GUAIFENESIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Guaifenesin, also known as glyceryl guaiacolate, sold under the brand name Mucinex, among others, is an expectorant medication taken by mouth and marketed as an aid to eliminate sputum from the respiratory tract. Chemically, it is an ether of guaiacol and glycerine. It may be used in combination with other medications. A 2014 study found that guaifenesin does not affect sputum volume in upper respiratory infections (the upper respiratory system includes most breathing parts above the lungs). In 2023, it was alleged to work by making airway secretions more liquid.
Side effects may include dizziness, sleepiness, skin rash, and nausea. While it has not been properly studied in pregnancy, it appears to be safe.
Guaifenesin has been used medically since at least 1933. It is available as a generic medication and over-the-counter (OTC). In 2023, it was the 291st most commonly prescribed medication in the United States, with more than 500,000 prescriptions. In 2023, the combination dextromethorphan/guaifenesin was the 315th most commonly prescribed medication in the United States, with more than 200,000 prescriptions.