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MedKoo Cat#: 463040 | Name: Amylocaine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Amylocaine was the first synthetic local anesthetic. It was synthesized and patented under the name Stovaine by Ernest Fourneau at the Pasteur Institute in 1903. It used to be used mostly in spinal anesthesia.

Chemical Structure

Amylocaine
Amylocaine
CAS#644-26-8 (freebase)

Theoretical Analysis

MedKoo Cat#: 463040

Name: Amylocaine

CAS#: 644-26-8 (freebase)

Chemical Formula: C14H21NO2

Exact Mass: 235.1572

Molecular Weight: 235.33

Elemental Analysis: C, 71.46; H, 9.00; N, 5.95; O, 13.60

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
644-26-8 (freebase); 532-59-2 (hydrochloride)
Synonym
Amyleine; Stovaine;
IUPAC/Chemical Name
1-(dimethylamino)-2-methylbutan-2-yl benzoate
InChi Key
FDMBBCOBEAVDAO-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H21NO2/c1-5-14(2,11-15(3)4)17-13(16)12-9-7-6-8-10-12/h6-10H,5,11H2,1-4H3
SMILES Code
CCC(CN(C)C)(OC(c1ccccc1)=O)C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 235.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Antipodal Views on Branding Amylocaine as Stovaine: Modesty or Political Correctness? Anesthesiology. 2019 Sep;131(3):579. doi: 10.1097/ALN.0000000000002940. PMID: 31408041. 2: Brum AM, van de Peppel J, Nguyen L, Aliev A, Schreuders-Koedam M, Gajadien T, van der Leije CS, van Kerkwijk A, Eijken M, van Leeuwen JPTM, van der Eerden BCJ. Using the Connectivity Map to discover compounds influencing human osteoblast differentiation. J Cell Physiol. 2018 Jun;233(6):4895-4906. doi: 10.1002/jcp.26298. Epub 2018 Jan 15. PMID: 29194609. 3: Stagnara J, Besse P, El Kebir S, Bordet MF. Symptoms associated with teething and response to three treatments, including homeopathic medicine: a multicenter prospective observational study among 190 French pediatricians. Minerva Pediatr. 2018 Dec;70(6):519-528. doi: 10.23736/S0026-4946.16.04585-0. Epub 2016 Sep 21. PMID: 27668452. 4: Bause GS. MBC stovaine pastilles. Anesthesiology. 2012 Mar;116(3):664. doi: 10.1097/ALN.0b013e31824e551f. PMID: 22354244. 5: Ionescu T. Rahianestezia generală.1909 [General rachianesthesia. 1909]. Chirurgia (Bucur). 2011 Jul-Aug;106(4):505-10; discussion 511-2. Romanian. PMID: 21991877. 6: Debue-Barazer C. Les implications scientifiques et industrielles du succès de la Stovaïne. Ernest Fourneau (1872-1949) et la chimie des médicaments en France [The effects of the success of the synthesis of Stovaïne in science and industry. Ernest Fourneau (1872-1949) and the transformation of the field of medicinal chemistry in France]. Gesnerus. 2007;64(1-2):24-53. French. PMID: 17982958. 7: Ball C, Westhorpe R. Local anaesthesia after cocaine. Anaesth Intensive Care. 2004 Apr;32(2):157. doi: 10.1177/0310057X0403200201. PMID: 15957711. 8: Hervás C, Cahisa M. Centenario de la raquianestesia en España: los primeros pasos (1899-1904) [Centenary of spinal anesthesia in Spain: first steps (1899-1904)]. Rev Esp Anestesiol Reanim. 2000 May;47(5):216-21. Spanish. PMID: 10902452. 9: Cortés Román C. Contribuciones de Carlos Roe León a la anestesia-analgesia obstétrica en España a principios del siglo XX [Contributions of Carlos Roe León to obstetric anesthesia and analgesia in Spain at the beginning of the 20th century]. Rev Esp Anestesiol Reanim. 1999 May;46(5):228; author reply 229. Spanish. PMID: 10379194. 10: Hirota K, Browne T, Appadu BL, Lambert DG. Do local anaesthetics interact with dihydropyridine binding sites on neuronal L-type Ca2+ channels? Br J Anaesth. 1997 Feb;78(2):185-8. doi: 10.1093/bja/78.2.185. PMID: 9068339. 11: Eisman M, Gallego M, Valcárcel M. Automatic determination of amylocaine and bromhexine by atomic absorption spectrometry. J Pharm Biomed Anal. 1993 Apr- May;11(4-5):301-5. doi: 10.1016/0731-7085(93)80021-r. PMID: 8357867. 12: Franco A, Cortés J, Vidal MI, Rabanal S. Una aportación a la historia de la raquiestrienoestovainización en España [History of rachianesthesia with strychnine and stovaine in Spain]. Rev Esp Anestesiol Reanim. 1993 Mar- Apr;40(2):101-2. Spanish. PMID: 8451466. 13: Polásek M, Gas B, Hirokawa T, Vacík J. Determination of limiting ionic mobilities and dissociation constants of some local anaesthetics. J Chromatogr. 1992 Apr 10;596(2):265-70. doi: 10.1016/0021-9673(92)85015-l. PMID: 1400841. 14: Vandewiele LJ. Dragées Bengué met Cocaïne. Geschiedkundig overzicht van de wettelijke bepalingen met betrekking tot de cocaïne [Dragées bengué with cocaine. Historic review of legislation concerning cocaine]. Verh K Acad Geneeskd Belg. 1991;53(5):531-46. Dutch. PMID: 1816703. 15: Marty P, Le Fichoux Y, Gari-Toussaint M, Ehrstein Y. Myiase furonculeuse à Cordylobia anthropophaga. Efficacité de l'association lindane-chlorhydrate d'amyléine [Cordylobia anthropophaga furuncular myiasis. Efficacy of a lindane- amyleine-chlorhydrate combination]. Presse Med. 1990 Jun 23;19(25):1196. French. PMID: 1694996. 16: Vaca Miguel JM. La raqui-estrieno-estovainización en España [Spinal anesthesia using a strychnine-stovaine combination in Spain]. Rev Esp Anestesiol Reanim. 1990 May-Jun;37(3):149-52. Spanish. PMID: 2202026. 17: Brownstein S, Liszauer AD, Jackson WB. Ocular complications of a topical methylene blue-vasoconstrictor-anesthetic preparation. Can J Ophthalmol. 1989 Dec;24(7):317-24. PMID: 2624913. 18: Schulte-Steinberg O. Beitrag zur Geschichte der Lokalanästhesie [The history of local anesthesia]. Anaesthesiol Reanim. 1989;14(5):285-9. German. PMID: 2684203. 19: Abdelaziz AA, el-Nakeeb MA. Sporicidal activity of local anaesthetics and their binary combinations with preservatives. J Clin Pharm Ther. 1988 Aug;13(4):249-56. doi: 10.1111/j.1365-2710.1988.tb00189.x. PMID: 3148619. 20: Abdelaziz AA, el-Nakeeb MA. Sporicidal activity of local anaesthetics and their binary combinations with preservatives. J Basic Microbiol. 1987;27(8):403-10. doi: 10.1002/jobm.3620270802. PMID: 3134539.