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Updating {{drugbox}} (changes to watched fields - added verified revid - updated 'ChemSpiderID_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (repo
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{{Short description|Chemical compound}}
{{about|the stimulant drug|the glycoprotein|Gp130}}
{{about|the stimulant drug|the glycoprotein|Gp130}}
{{Drugbox
{{Drugbox
⚫
| verifiedrevid = 451605938
| Watchedfields = changed
⚫
| verifiedrevid = 449581162
| IUPAC_name = 2-phenyl-5,5-dimethylmorpholine
| IUPAC_name = 2-phenyl-5,5-dimethylmorpholine
| image = G-130_structure.png
| image = G-130_structure.png
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_DE = NpSG
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_UK = PSA
| 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 =


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


<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 42013-48-9
| CAS_number = 42013-48-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 785F2C727T
| ATC_prefix =
| ATC_prefix =
| ATC_suffix =
| ATC_suffix =
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| DrugBank =
| ChemSpiderID = 88190
| StdInChI = 1S/C12H17NO/c1-12(2)9-14-11(8-13-12)10-6-4-3-5-7-10/h3-7,11,13H,8-9H2,1-2H3
| StdInChIKey = KJUOROGOOZJYAI-UHFFFAOYSA-N


<!--Chemical data-->
<!--Chemical data-->
| C=12 | H=17 | N=1 | O=1
| C=12 | H=17 | N=1 | O=1
| smiles = CC1(C)NCC(OC1)C2=CC=CC=C2
| molecular_weight = 191.269 g/mol
| smiles = c1ccccc1C(CN2)OCC2(C)C
}}
}}


'''G-130''' ('''GP-130''', '''2-Phenyl-5,5-dimethyltetrahydro-1,4-oxazine''')<ref>{{Cite patent|GB|1336732}} - Diethanolamine Derivatives.</ref> is a drug with [[stimulant]] and [[anorectic]] effects, related to [[phenmetrazine]].<ref name="pmid4740767">{{cite journal |author=Fanelli O |title=Pharmacological and toxicological study of a new psychotropic stimulant: the 2-phenyl-5-dimethyl-tetrahydro-1,4-oxazine, in comparison with d,l-amphetamine, phenmetrazine and pemoline-Mg |journal=Arzneimittel-Forschung |volume=23 |issue=6 |pages=810–6 |year=1973 |month=June |pmid=4740767 |doi= |url=}}</ref><ref name="pmid4479774">{{cite journal |author=Fanelli O, Mazzoncini V, Ferri S |title=Toxicological and teratological study of 2-phenyl-5,5-dimethyl-tetrahydro-1,4-oxazine hydrochloride (G 130), a psychostimulant drug |journal=Arzneimittel-Forschung |volume=24 |issue=10 |pages=1627–32 |year=1974 |month=October |pmid=4479774 |doi= |url=}}</ref><ref name="pmid4480283">{{cite journal |author=Fanelli O, Mazzoncini V, Trallori L |title=Antagonism of psychostimulant 2-phenyl-5,5-dimethyl-tetrahydro-1,4-oxazine hydrochloride (G 130) to central nervous system depressing drugs. Monoamine oxidase inhibitory activity and norepinephrine and serotonin induced changes. Comparison with dL-amphetamine |journal=Arzneimittel-Forschung |volume=24 |issue=12 |pages=2025–9 |year=1974 |month=December |pmid=4480283 |doi= |url=}}</ref>
'''G-130''' ('''GP-130''', '''2-Phenyl-5,5-dimethyltetrahydro-1,4-oxazine''')<ref name=patent>{{Cite patent|country=GB|number=1336732|pubdate=1973-11-07|title=Diethanolamine derivatives|assign1=Instituto Gentili SPA}}</ref> is a drug with [[stimulant]] and [[anorectic]] effects, related to [[phenmetrazine]].<ref name="pmid4740767">{{cite journal | vauthors = Fanelli O | title = Pharmacological and toxicological study of a new psychotropic stimulant: the 2-phenyl-5-dimethyl-tetrahydro-1,4-oxazine, in comparison with d,l-amphetamine, phenmetrazine and pemoline-Mg | journal = Arzneimittel-Forschung | volume = 23 | issue = 6 | pages = 810–816 | date = June 1973 | pmid = 4740767 }}</ref><ref name="pmid4479774">{{cite journal | vauthors = Fanelli O, Mazzoncini V, Ferri S | title = Toxicological and teratological study of 2-phenyl-5,5-dimethyl-tetrahydro-1,4-oxazine hydrochloride (G 130), a psychostimulant drug | journal = Arzneimittel-Forschung | volume = 24 | issue = 10 | pages = 1627–1632 | date = October 1974 | pmid = 4479774 }}</ref><ref name="pmid4480283">{{cite journal | vauthors = Fanelli O, Mazzoncini V, Trallori L | title = Antagonism of psychostimulant 2-phenyl-5,5-dimethyl-tetrahydro-1,4-oxazine hydrochloride (G 130) to central nervous system depressing drugs. Monoamine oxidase inhibitory activity and norepinephrine and serotonin induced changes. Comparison with dL-amphetamine | journal = Arzneimittel-Forschung | volume = 24 | issue = 12 | pages = 2025–2029 | date = December 1974 | pmid = 4480283 }}</ref>


==Structural analogs ==
==Structural analogs ==
Compounds related to G 130 and [[radafaxine]] were synthesized that behave as combined [[Reuptake inhibitor|inhibitors of monoamine uptake]] and [[nAChR]]s.<ref>{{Cite pmid|21319801}}</ref>
Compounds related to G-130 and [[radafaxine]] were synthesized that behave as combined [[Reuptake inhibitor|inhibitors of monoamine uptake]] and [[nicotinic acetylcholine receptor]]s.<ref>{{cite journal | vauthors = Carroll FI, Muresan AZ, Blough BE, Navarro HA, Mascarella SW, Eaton JB, Huang X, Damaj MI, Lukas RJ | display-authors = 6 | title = Synthesis of 2-(substituted phenyl)-3,5,5-trimethylmorpholine analogues and their effects on monoamine uptake, nicotinic acetylcholine receptor function, and behavioral effects of nicotine | journal = Journal of Medicinal Chemistry | volume = 54 | issue = 5 | pages = 1441–1448 | date = March 2011 | pmid = 21319801 | pmc = 3048909 | doi = 10.1021/jm1014555 }}</ref>
==Synthesis==
--> C1=C(Cl)C=CC=C1C2OCC(C)(C)N(CC)C2C
[[File:G-130 synthesis.svg|thumb|center|500px|Patent:<ref name=patent/> Spanish [[Fepradinol]] patent:<ref>ES508287 (application number) idem {{Cite patent|ES|8300676}} (1983 to Elmu Sa).</ref>]]
Ex 1: 2 moles of 2-methyl-2-aminopropanol ([[aminomethyl propanol]]) ('''1''') is reacted with 1 moles of [[styrene oxide]] (phenyloxirane) [96-09-3] ('''2''') in 0.2 mole water.


Ex 2: [[Fepradinol]] [36981-91-6] [63075-47-8] ('''3''') is treated with acid, to cyclize to the morpholine ring.
⚫
==See also==

⚫
== See also ==
* [[2-Phenyl-3,6-dimethylmorpholine]]
* [[2-Phenyl-3,6-dimethylmorpholine]]
* [[3-Fluorophenmetrazine]]
* [[Phendimetrazine]] (2-Phenyl-3,4-dimethylmorpholine)
* [[4-Methylphenmetrazine]]
* [[Phendimetrazine]]
* [[Manifaxine]]
* [[Manifaxine]]
* [[Radafaxine]]


==References==
== References ==
{{reflist}}
<references/>


{{stimulants}}
{{stimulants}}


[[Category:Stimulants]]
[[Category:Stimulants]]
[[Category:Morpholines]]
[[Category:Phenylmorpholines]]
[[Category:Designer drugs]]



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