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Revision as of 22:00, 30 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'ChEBI_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report errors or bugs)← Previous edit Latest revision as of 08:48, 14 November 2023 edit undoSolid Thight (talk | contribs)52 editsNo edit summaryTag: Visual edit 
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{{short description|Chemical compound}}
{{Unreferenced stub|auto=yes|date=December 2009}}
{{Drugbox {{Drugbox
| verifiedrevid = 415529194 | verifiedrevid = 461769300
| IUPAC_name = 1-cyclohexylaminopropan-2-yl benzoate | IUPAC_name = 1-cyclohexylaminopropan-2-yl benzoate
| image = Hexylcaine.PNG | image = Hexylcaine Structure.svg

<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =
| pregnancy_category = | pregnancy_category =
| legal_status = | legal_status =
| routes_of_administration = | routes_of_administration =

<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
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| metabolism = | metabolism =
| elimination_half-life = <10 minutes | elimination_half-life = <10 minutes

<!--Identifiers--> <!--Identifiers-->
| IUPHAR_ligand = 7196
| CASNo_Ref = {{cascite|correct|CAS}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 532-77-4 | CAS_number = 532-77-4
| ATC_prefix = none | ATC_prefix = None
| ATC_suffix = | ATC_suffix =
| ATC_supplemental = | ATC_supplemental =
| PubChem = 10770 | PubChem = 10770
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = APRD01014 | DrugBank = DB00473
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10315 | ChemSpiderID = 10315
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| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1197 | ChEMBL = 1197

<!--Chemical data--> <!--Chemical data-->
| C=16 | H=23 | N=1 | O=2 | C=16 | H=23 | N=1 | O=2
| molecular_weight = 261.359 g/mol
| smiles = O=C(OC(CNC1CCCCC1)C)c2ccccc2 | smiles = O=C(OC(CNC1CCCCC1)C)c2ccccc2
| InChI = 1/C16H23NO2/c1-13(12-17-15-10-6-3-7-11-15)19-16(18)14-8-4-2-5-9-14/h2,4-5,8-9,13,15,17H,3,6-7,10-12H2,1H3
| InChIKey = DKLKMKYDWHYZTD-UHFFFAOYAY
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C16H23NO2/c1-13(12-17-15-10-6-3-7-11-15)19-16(18)14-8-4-2-5-9-14/h2,4-5,8-9,13,15,17H,3,6-7,10-12H2,1H3 | StdInChI = 1S/C16H23NO2/c1-13(12-17-15-10-6-3-7-11-15)19-16(18)14-8-4-2-5-9-14/h2,4-5,8-9,13,15,17H,3,6-7,10-12H2,1H3
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| StdInChIKey = DKLKMKYDWHYZTD-UHFFFAOYSA-N | StdInChIKey = DKLKMKYDWHYZTD-UHFFFAOYSA-N
}} }}
'''Hexylcaine hydrochloride''', also called '''cyclaine''' (]) or '''osmocaine''', is a short-acting ]. It acts by inhibiting ] conduction. Overdose can lead to ], ], ] around the mouth and tongue, ]s, ], and decreased heart function. '''Hexylcaine hydrochloride''', also called '''cyclaine''' (]) or '''osmocaine''', is a short-acting ]. It acts by inhibiting ] conduction. Overdose can lead to ], ], ] around the mouth and tongue, ]s, ], and decreased heart function.<ref name="pmid13620024">{{cite journal | vauthors = Spellberg MA | title = Hexylcaine (cyclaine) as topical anesthetic in gastroscopy and esophagoscopy | journal = Gastroenterology | volume = 36 | issue = 1 | pages = 120–1 | date = January 1959 | pmid = 13620024 | doi = 10.1016/S0016-5085(59)80102-5| url = }}</ref>
==Synthesis==
]
The ] between ] ('''1''') and ] gives 1-Cyclohexylamino-2-propanol ('''2'''). Treatment with ] gives the ester, completing the synthesis of Hexylcaine ('''3''').{{Citation needed|date=November 2023}}


==References==
{{Reflist}}
{{Local anesthetics}} {{Local anesthetics}}


] ]
] ]
]



{{nervous-system-drug-stub}} {{nervous-system-drug-stub}}

Latest revision as of 08:48, 14 November 2023

Chemical compound Pharmaceutical compound
Hexylcaine
Clinical data
ATC code
  • None
Pharmacokinetic data
Elimination half-life<10 minutes
Identifiers
IUPAC name
  • 1-cyclohexylaminopropan-2-yl benzoate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H23NO2
Molar mass261.365 g·mol
3D model (JSmol)
SMILES
  • O=C(OC(CNC1CCCCC1)C)c2ccccc2
InChI
  • InChI=1S/C16H23NO2/c1-13(12-17-15-10-6-3-7-11-15)19-16(18)14-8-4-2-5-9-14/h2,4-5,8-9,13,15,17H,3,6-7,10-12H2,1H3
  • Key:DKLKMKYDWHYZTD-UHFFFAOYSA-N
  (verify)

Hexylcaine hydrochloride, also called cyclaine (Merck) or osmocaine, is a short-acting local anesthetic. It acts by inhibiting sodium channel conduction. Overdose can lead to headache, tinnitus, numbness and tingling around the mouth and tongue, convulsions, inability to breathe, and decreased heart function.

Synthesis

Synthesis: Patent:

The reductive amination between 1-Amino-2-propanol (1) and cyclohexanone gives 1-Cyclohexylamino-2-propanol (2). Treatment with benzoyl chloride gives the ester, completing the synthesis of Hexylcaine (3).

References

  1. Spellberg MA (January 1959). "Hexylcaine (cyclaine) as topical anesthetic in gastroscopy and esophagoscopy". Gastroenterology. 36 (1): 120–1. doi:10.1016/S0016-5085(59)80102-5. PMID 13620024.
  2. Cope, Arthur C.; Hancock, Evelyn M. (1944). "1-Alkylamino-2-propanols and their p-Nitro- and p-Aminobenzoates". Journal of the American Chemical Society 66 (9): 1453–1456. doi:10.1021/ja01237a010.
  3. "Local Anesthetics". New England Journal of Medicine. 263 (19): 963–965.1960. doi:10.1056/NEJM196011102631912.
  4. Cope Arthur C, U.S. patent 2,486,374 (1949 to Sharp & Dohme Inc).
Local anesthetics (primarily sodium channel blockers) (N01B)
Esters by acid
Aminobenzoic
Benzoic
ArCO2- (not para-amino or Ph)
Amides
Combinations
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