{"Abbreviation":"BDO","Aliases":["Butane-1,4-diol","Tetramethylene glycol","1,4-Butylene glycol","1,4-Dihydroxybutane","1,4-Tetramethylene glycol","Tetramethylene 1,4-diol","Sucol B","DIOL 14B","1,4-BD","Agrisynth B1D"],"Boiling Point":"446 °","CAS":"110-63-4","ChEBI":"CHEBI:41189","ChEMBL":"CHEMBL171623","ChemicalClasses":["alcohol"],"Chirality":"achiral","Classes":null,"Color/Form":"Colorless, oily liquid","Decomposition":"When heated to decomposition it emits acrid smoke and fumes.","Density":"1.017 at 68 °F (USCG, 1999) - Denser than water; will sink g/cm\u003csup\u003e3\u003c/sup\u003e","Drug Warnings":"15 or 30 g of 1,4-butanediol (0.21 or 0.43 g/kg bw) was rectally administered to 7 patients. After 10 to 20 minutes, the patients became /comatose/ after deep unconsciousness, miosis and complete areflexia and this condition continued for 1 to 16 hr. Two of them died within 72 hours after the administration, but other five patients recovered naturally or after treatment with analeptic. Sustained disorder was not observed. Renal disorder was found on two /dead/ patients.","DrugClasses":[],"EINECS":"203-786-5","Erowid Experience Reports":[{"Id":"100079","Title":"Intense Pain in My Abdomen"},{"Id":"10082","Title":"1,4-B Is Not a Toy"},{"Id":"101021","Title":"Extremely Addictive"},{"Id":"10449","Title":"Not All People Experience Addiction"},{"Id":"108903","Title":"Extremely Dangerous"},{"Id":"114173","Title":"SUPER Danger"},{"Id":"116617","Title":"Terrible Anxiety and Depression Till This Day"},{"Id":"12872","Title":"Good and a Little Too Intense"},{"Id":"116974","Title":"Daily Usage Resulting in Muscle Injury"},{"Id":"13977","Title":"A Wife's Point of View"},{"Id":"14352","Title":"Toxicity After Infrequent Use"},{"Id":"13412","Title":"For Growth Hormone"},{"Id":"16093","Title":"During Withdrawal Wishing I Was Dead!"},{"Id":"16843","Title":"Not Addictive, My Big Ol' Butt"},{"Id":"16276","Title":"Near Death Experience"},{"Id":"18264","Title":"Tips for Withdrawing"},{"Id":"1920","Title":"Withdrawal Symptoms"},{"Id":"1927","Title":"A $6,000 Bill"},{"Id":"1929","Title":"1,4-Butanediol Toxicity?"},{"Id":"22604","Title":"Life Force"},{"Id":"2423","Title":"A Multifaceted Substance"},{"Id":"29274","Title":"Pharmacological Error"},{"Id":"29450","Title":"Addictive? Yes and No"},{"Id":"30129","Title":"$25k and Near Fatal Outcome"},{"Id":"3317","Title":"Definitely addictive!"},{"Id":"3852","Title":"Fairly Neutral Exp with BDO"}],"Esters":["dipropionate"],"European Community (EC) Number":"203-786-5","Flash Point":"247 °F (NTP, 1992)","HMDB ID":"HMDB0244201","HeavyAtomCount":6,"IUPACName":"butane-1,4-diol","InChI":"InChI=1S/C4H10O2/c5-3-1-2-4-6/h5-6H,1-4H2","InChIKey":"WERYXYBDKMZEQL-UHFFFAOYSA-N","Melting Point":"61 °","MolecularFormula":"C\u003csub\u003e4\u003c/sub\u003eH\u003csub\u003e10\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e","MolecularWeight":"90.12 g/mol","Odor":"Almost odorless","Physical Description":"1,4-butanediol appears as odorless colorless liquid or solid (depending upon temperature). (USCG, 1999)","PrevSalts":[],"PubChemId":8064,"Record Description":["1,4-butanediol appears as odorless colorless liquid or solid (depending upon temperature). (USCG, 1999)","Butane-1,4-diol is a butanediol that is butane in which one hydrogen of each of the methyl groups is substituted by a hydroxy group. A colourless, water-miscible, viscous liquid at room temperature (m.p. 16℃) with a high boiling point (230℃), it is mainly used for the production of other organic chemicals, particularly the solvent oxolane (also known as tetrahydrofuran or THF). It has a role as a neurotoxin, a protic solvent and a prodrug. It is a butanediol and a glycol.","See also: Polybutester (monomer of); Dilinoleic acid/butanediol copolymer (monomer of).","Butane-1,4-diol is a butanediol that is butane in which one hydrogen of each of the methyl groups is substituted by a hydroxy group. A colourless, water-miscible, viscous liquid at room temperature (m.p. 16℃) with a high boiling point (230℃), it is mainly used for the production of other organic chemicals, particularly the solvent oxolane (also known as tetrahydrofuran or THF). It has a role as a neurotoxin, a protic solvent and a prodrug. It is a butanediol and a glycol.","Wikipedia|List of designer drugs|Sedatives|GHB analogues"],"RefCount":3,"References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/1,4-Butanediol","Name":"1,4-Butanediol","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q161521","Name":"1,4-Butanediol","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB01955","Name":"1,4-Butanediol","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/8064","Name":"1,4-Butanediol","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL171623","Name":"1,4-Butanediol","Sub":false}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:41189","Name":"1,4-Butanediol","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=110-63-4","Name":"1,4-Butanediol","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0244201","Name":"1,4-Butanediol","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/7XOO2LE6G3","Name":"1,4-Butanediol","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID2024666","Name":"1,4-Butanediol","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 8064, 1,4-Butanediol. Accessed June 26, 2025. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/8064\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/8064\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. 1,4-Butanediol. UNII: 7XOO2LE6G3. Global Substance Registration System. Accessed June 26, 2025. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/7XOO2LE6G3\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/7XOO2LE6G3\u003c/a\u003e"],"SMILES":"C(CCO)CO","Solubility":"greater than or equal to 100 mg/mL at 73 °F (NTP, 1992)","Stability/Shelf Life":"Stable under recommended storage conditions.","StoreUNII":["7XOO2LE6G3"],"StructureBase64":"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","Subjective Effects":null,"Therapeutic Uses":"/EXPL THER/: Two studies have been identified concerning the use of 1,4-butanediol as a sedative. The favorable sedative effect of 4-hydroxybutyric acid-sodium in the treatment of intensive-care patients had the disadvantage that the patients were given too much sodium (1g sodium hydroxybutyrate is equivalent to 180 mg sodium). Attempts were therefore made to use the parent compound, 1,4-butanediol , directly. A single iv injection of ...1,4-butanediol... /was/ given to each of 3 artificially ventilated patients (19 to 43 years of age) caused 2 of the patients to fall asleep for 60 minutes and 3 hours, respectively. In 1 of these patients, no pain occurred for 45 to 60 minutes after the injection. The patients fell asleep 5 to 10 minutes after the injection. For 2.5 to 3 hours after administration, the tendon reflexes were absent. Cardiovascular and hematological parameters, liver and kidney function, body temperature and swallowing reflex were unaffected. The plasma 4-hydroxybutyric acid level was 150 to 180 ug/mL in all 3 patients 20 to 30 minutes after the injection. Iv injection of /a lesser dose/ caused only a slight reduction in spontaneous movement, in particular, eye movements (1 patient studied). Three further patients (23 to 40 years), 1 patient with cerebral contusion, the other two patients with no neurological abnormalities), were given an initial dose ...iv followed by an iv infusion ...for 38 or 68 hours... . The infusions had to be briefly interrupted due to medical or technical problems, and/or additional bolus injections were given. 1,4-Butanediol caused sleep as well as loss of swallowing and tendon reflexes during the entire infusion period. In 2 of the patients, restlessness occurred during infusion, and in 1, periodic contractions of the muscles of the extremities. Changes in liver and kidney function and in hematological parameters were not seen in the patients either during or at the end of infusion, nor were any treatment-related neurological effects observed.","Title":"1,4-Butanediol","UNII":"7XOO2LE6G3","Wikidata":"Q161521","Wikipedia":"1,4-Butanediol","XLogP":-0.8}