Camylofin: Difference between revisions

{{Short description|Chemical compound}}

{{

| Verifiedfields = changed

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| IUPAC_name = 2-[2-(diethylamino)ethylamino]-2-phenylacetate

| image = Camylofin.png

<!--Clinical data-->

| tradename =

| Drugs.com = {{drugs.com|international|camylofin}}

| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->

| pregnancy_US = <!-- A / B / C / D / X -->

| pregnancy_category=

| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->

| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->

| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->

| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->

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| bioavailability

| protein_bound

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<!--Identifiers-->

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 54-30-8

| ATC_prefix = A03

| ATC_suffix = AA03

| PubChem = 5902

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 253592

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 5691

| synonyms = Acamylophenine

<!--Chemical data-->

| =

| smiles = O=C(OCCC(C)C)C(NCCN(CC)CC)c1ccccc1

| = {{||}}

| StdInChI = 1S/C19H32N2O2/c1-5-21(6-2)14-13-20-18(17-10-8-7-9-11-17)19(22)23-15-12-16(3)4/h7-11,16,18,20H,5-6,12-15H2,1-4H3

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = RYOOHIUJEJZCFT-UHFFFAOYSA-N

'''Camylofin''' is an [[antimuscarinic]].

Camylofin is a [[smooth muscle]] relaxant with both [[anticholinergic]] action and direct [[smooth muscle]] action. Anticholinergic action is produced by inhibiting the binding of [[acetylcholine]] to [[muscarinic receptors]], but the action is less pronounced.{{cn|date=April 2021}} Direct smooth muscle relaxation is achieved by inhibiting [[phosphodiesterase]] type IV, which leads to increased [[cyclic AMP]] and eventually reduced [[cytosolic]] calcium. Thus camylofin has a comprehensive action to relieve smooth muscle [[spasm]]. It is used to treat stomach ache in infants and children. Usually it is given in combination with [[paracetamol]] to treat stomach ache, as well as [[pyrexia]].<ref>{{cite journal | vauthors = Sarbhjit K, Bajwa SK, Parmjit K, Surinder B | title = To compare the effect of camylofin dihydrochloride (anafortin) with combination of valethamate bromide (epidosin) and hyoscine butyl-N-bormide (buscopan) on cervical dilation | journal = Journal of Clinical and Diagnostic Research | volume = 7 | issue = 9 | pages = 1897–9 | date = September 2013 | pmid = 24179892 | pmc = 3809631 | doi = 10.7860/JCDR/2013/6231.3345 }}</ref>

==Synthesis==

[[File:Camylofin synthesis.svg|thumb|center|500px|Synthesis:<ref>Bruzzese, Tiberio; Crescenzi, Elda (1966). "N-Aminoalkyl-α-aminoacids and Their Corresponding Ethyl Esters". Journal of Pharmaceutical Sciences. 55 (7): 737–740. doi:10.1002/jps.2600550717. </ref><ref>Szarvasi, E. et al, Bull. Soc. Chim. Fr., 1957, 1019.</ref> Patents:<ref>Brock Norbert, Kuhas Engelbert, & Schmeisser Martin, {{US patent|2665300}} (1954 to Asta Medica AG).</ref><ref>Martin Dr-Chem Schmeisser, Engelbert Dr Phil Kuehas, Norbert Dr Med Brock, DE842206 (1952 to Asta Werke Ag Chem Fab).</ref><ref>, GB688331 (1953 to Asta Medica AG).</ref> Metamizole salt patents:<ref>, GB782068 (1957 to Asta Medica AG).</ref><ref>Kuhas Engelbert, Brock Norbert, & Arnold Herbert, CA566251 (1958 to Asta Medica AG).</ref><ref>Arnold Herbert, Kuhas Engelbert, & Brock Norbert, {{US patent|2857395}} (1958).</ref>]]

The [[Hell–Volhard–Zelinsky halogenation]] on phenylacetic acid [103-82-2] ('''1''') gives 2-Bromo-2-phenylacetyl bromide, [https://pubchem.ncbi.nlm.nih.gov/compound/15621041 CID:15621041] ('''2'''). Treatment with [[isoamyl alcohol]] [123-51-3] gives 3-methylbutyl bromo(phenyl)acetate [92018-48-9] ('''3'''). Alkylation with N,N-Diethylethylenediamine [100-36-7] ('''4''') completed the synthesis of ''Camylofin'' ('''5''').

== References ==

{{Reflist|2}}

{{Muscarinic acetylcholine receptor modulators}}

[[Category:]]

[[Category:Muscarinic antagonists]]