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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
⚫
| IUPAC_name = (1''R'')-''N''-Ethyl-2-phenyl-1-[(2''R'')-tetrahydrofuran-2-yl]ethanamine
| verifiedrevid = 443223982
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| IUPAC_name = (1''R'')-​''N''-​ethyl-​2-​phenyl-​1-​[(2''R'')-​tetrahydrofuran-​2-​yl]​ethanamine
| image = Zylofuramine.svg
| image = Zylofuramine.svg


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


<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
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| metabolism =
| metabolism =
| elimination_half-life =
| elimination_half-life =
| excretion =
| excretion =


<!--Identifiers-->
<!--Identifiers-->
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<!--Chemical data-->
<!--Chemical data-->
| C=15 | H=23 | N=1
| C=14 | H=21 | N=1 | O=1
| molecular_weight = 219.32264 g/mol
| smiles = O2[C@@H]([C@H](NCC)Cc1ccccc1)CCC2
| smiles = O2[C@@H]([C@H](NCC)Cc1ccccc1)CCC2
| InChI = 1/C14H21NO/c1-2-15-13(14-9-6-10-16-14)11-12-7-4-3-5-8-12/h3-5,7-8,13-15H,2,6,9-11H2,1H3/t13-,14-/m1/s1
| InChIKey = DOFCLOLKFGSRTG-ZIAGYGMSBA
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C14H21NO/c1-2-15-13(14-9-6-10-16-14)11-12-7-4-3-5-8-12/h3-5,7-8,13-15H,2,6,9-11H2,1H3/t13-,14-/m1/s1
| StdInChI = 1S/C14H21NO/c1-2-15-13(14-9-6-10-16-14)11-12-7-4-3-5-8-12/h3-5,7-8,13-15H,2,6,9-11H2,1H3/t13-,14-/m1/s1
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'''Zylofuramine'''<ref>US Patent 3091621</ref> is a [[stimulant]] drug. It was developed in 1961,<ref>{{Cite doi|10.1021/jm01236a010}}</ref> and was intended for use as an [[appetite suppressant]] and for the treatment of [[senile dementia]] in the elderly, but there is little information about it and it does not appear to have ever been marketed.<ref>Harris LS, Clarke RL, Dembinski JR. Alpha-Benzyltetrahydrofurfurylamines - A new series of Psychomotor Stimulants. III. The Pharmacology of D-Threo Alpha-Benzyl-N-Ethyltetrahydrofurfurylamine (Zylofuramine). ''Archives Internationales de Pharmacodynamie et de Therapie''. 1963 Dec 1;146:392-405.</ref>
'''Zylofuramine'''<ref name=patent>{{ cite patent | country = US | status = patent | number = 3091621 | inventor = Clarke RL | gdate = 1963-05-28 | assign1 = Sterling Drugs | title = Alpha-Aryl or Aralkyl Tetrahydrofurfurylamines }}</ref> is a [[stimulant]] drug. It was developed in 1961,<ref name=Clarke>{{cite journal | vauthors = Clarke RL, Harris LS | title = α-Benzyltetrahydrofurfurylamines -- A New Series of Psychomotor Stimulants. I | journal = Journal of Medicinal and Pharmaceutical Chemistry | volume = 5 | issue = 1 | pages = 77–95 | date = January 1962 | pmid = 14046619 | doi = 10.1021/jm01236a010 }}</ref><ref>{{cite journal | vauthors = Clarke RL, Tullar BF, Harris LS | title = α-Benzyltetrahydrofurfurylamines -- A New Series of Psychomotor Stimulants. II. Resolution of Isomers | journal = Journal of Medicinal and Pharmaceutical Chemistry | volume = 5 | issue = 2 | pages = 362–72 | date = March 1962 | pmid = 14051912 | doi = 10.1021/jm01237a014 }}</ref> and was intended for use as an [[appetite suppressant]] and for the treatment of [[senile dementia]] in the elderly, but there is little information about it and it does not appear to have ever been marketed.<ref>{{cite journal | vauthors = Harris LS, Clarke RL, Dembinski JR | title = α-Benzyltetrahydrofurfurylamines -- A New Series of Psychomotor Stimulants. III. The Pharmacology of D-Threo α-Benzyl-N-Ethyltetrahydrofurfurylamine (Zylofuramine) | journal = Archives Internationales de Pharmacodynamie et de Therapie | volume = 146 | pages = 392–405 | date = December 1963 | pmid = 14099588 }}</ref>


Zylofuramine is legal throughout the world. Its [[chemical structure]] has a vague similarity to other N-ethyl substituted stimulant drugs such as [[ethylamphetamine]], but its structure would probably not be close enough for it to be considered a [[Designer drug|controlled substance analogue]].
Its [[chemical structure]] has a similarity to other ''N''-ethyl substituted stimulant drugs such as [[ethylamphetamine]] and [[N-Ethylhexedrone]].

==Synthesis==
:[[File:Zylofuramine synthesis.svg|upright=2]]
The [[Grignard reaction]] of benzylmagnesium bromide (1) and the [[imine]] of [[furfural]] and [[ethylamine]], N-ethylfuran-2-methaneimine (2), gives the [[amine]] derivative (3). [[Hydrogenation]] using a [[Raney nickel]] catalyst yields zylofuramine.<ref name=patent/><ref name=Clarke/>


== References ==
== References ==
{{Reflist|2}}
{{Reflist}}


{{Stimulants}}
{{Stimulants}}
{{Anorectics}}
{{Anorectics}}
{{Monoamine releasing agents}}
{{Adrenergics}}
{{Dopaminergics}}
{{Phenethylamines}}
{{Phenethylamines}}




[[Category:Stimulants]]
[[Category:Stimulants]]
[[Category:Tetrahydrofurans]]
[[Category:Tetrahydrofurans]]
[[Category:Phenethylamines]]
[[Category:Phenethylamines]]
[[Category:Norepinephrine-dopamine releasing agents]]


⚫
{{nervous-system-drug-stub}}

⚫
{{gastrointestinal-drug-stub}}

Latest revision as of 14:18, 17 July 2024

Zylofuramine
Clinical data
ATC code
  • none
Identifiers
  • (1R)-N-Ethyl-2-phenyl-1-[(2R)-tetrahydrofuran-2-yl]ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H21NO
Molar mass219.328 g·mol−1
3D model (JSmol)
  • O2[C@@H]([C@H](NCC)Cc1ccccc1)CCC2
  • InChI=1S/C14H21NO/c1-2-15-13(14-9-6-10-16-14)11-12-7-4-3-5-8-12/h3-5,7-8,13-15H,2,6,9-11H2,1H3/t13-,14-/m1/s1 checkY
  • Key:DOFCLOLKFGSRTG-ZIAGYGMSSA-N checkY

Zylofuramine[1] is a stimulant drug. It was developed in 1961,[2][3] and was intended for use as an appetite suppressant and for the treatment of senile dementia in the elderly, but there is little information about it and it does not appear to have ever been marketed.[4]

Its chemical structure has a similarity to other N-ethyl substituted stimulant drugs such as ethylamphetamine and N-Ethylhexedrone.

Synthesis

[edit]

The Grignard reaction of benzylmagnesium bromide (1) and the imine of furfural and ethylamine, N-ethylfuran-2-methaneimine (2), gives the amine derivative (3). Hydrogenation using a Raney nickel catalyst yields zylofuramine.[1][2]

References

[edit]
  1. ^ a b US patent 3091621, Clarke RL, "Alpha-Aryl or Aralkyl Tetrahydrofurfurylamines", issued 1963-05-28, assigned to Sterling Drugs 
  2. ^ a b Clarke RL, Harris LS (January 1962). "α-Benzyltetrahydrofurfurylamines -- A New Series of Psychomotor Stimulants. I". Journal of Medicinal and Pharmaceutical Chemistry. 5 (1): 77–95. doi:10.1021/jm01236a010. PMID 14046619.
  3. ^ Clarke RL, Tullar BF, Harris LS (March 1962). "α-Benzyltetrahydrofurfurylamines -- A New Series of Psychomotor Stimulants. II. Resolution of Isomers". Journal of Medicinal and Pharmaceutical Chemistry. 5 (2): 362–72. doi:10.1021/jm01237a014. PMID 14051912.
  4. ^ Harris LS, Clarke RL, Dembinski JR (December 1963). "α-Benzyltetrahydrofurfurylamines -- A New Series of Psychomotor Stimulants. III. The Pharmacology of D-Threo α-Benzyl-N-Ethyltetrahydrofurfurylamine (Zylofuramine)". Archives Internationales de Pharmacodynamie et de Therapie. 146: 392–405. PMID 14099588.
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