Phentermine

Template:Short description Template:Use dmy dates Template:Cs1 config Template:Main other {{#invoke:Infobox|infobox}}Template:Template other{{#invoke:TemplatePar |check |template=Template:Infobox_drug |all= |opt= pronounce= pronounce_ref= pronounce_comment= ATC_prefix= ATC_suffix= ATC_supplemental= ATCvet= biosimilars= CAS_number_Ref= CAS_number= CAS_supplemental= ChEBI= ChEBI_Ref= ChEMBL_Ref= ChEMBL= ChemSpiderID= ChemSpiderID_Ref= chirality= class= container_only= DailyMedID= data_page= DrugBank_Ref= DrugBank= Drugs.com= duration_of_action= INN= INN_EMA= IUPAC_name= IUPHAR_ligand= KEGG_Ref= KEGG= MedlinePlus= NIAID_ChemDB= PDB_ligand= PubChemSubstance= PubChem= StdInChIKey_Ref= StdInChIKey= StdInChI_Ref= StdInChI_comment= StdInChI= UNII_Ref= UNII= DTXSID= Verifiedfields= Watchedfields= addiction_liability= alt2= altL= altR= alt= bioavailability= boiling_high= boiling_notes= boiling_point= captionLR= caption= caption2= charge= chemical_formula= chemical_formula_ref= chemical_formula_comment= class1= class2= class3= class4= class5= class6= component1= component2= component3= component4= component5= component6= density= density_notes= dependency_liability= drug_name= elimination_half-life= engvar= excretion= image2= imageL= imageR= image= image_class= image_class2= image_classL= image_classR= Jmol= legal_AU= legal_BR= legal_CA= legal_DE= legal_EU= legal_NZ= legal_UK= legal_UN= legal_US= legal_AU_comment= legal_BR_comment= legal_CA_comment= legal_DE_comment= legal_UK_comment= legal_NZ_comment= legal_US_comment= legal_UN_comment= legal_EU_comment= legal_status= licence_CA= licence_EU= licence_US= license_CA= license_EU= license_US= mab_type= melting_high= melting_notes= melting_point= metabolism= metabolites= molecular_weight= molecular_weight_round= molecular_weight_unit= molecular_weight_ref= molecular_weight_comment= onset= pregnancy_AU= pregnancy_AU_comment= pregnancy_category= protein_bound= routes_of_administration= SMILES= smiles= solubility= sol_units= source= specific_rotation= synonyms= target= tradename= type= vaccine_type= verifiedrevid= width2= widthL= widthR= width= AAN= BAN= JAN= USAN= source_tissues= target_tissues= receptors= agonists= antagonists= precursor= biosynthesis= gt_target_gene= gt_vector= gt_nucleic_acid_type= gt_editing_method= gt_delivery_method= sec_combustion= Ac=Ag=Al=Am=Ar=As=At=Au=B=Ba=Be=Bh=Bi=Bk=Br=C=Ca=Cd=Ce=Cf=Cl=Cm=Cn=Co=Cr=Cs=Cu= D=Db=Ds=Dy=Er=Es=Eu=F=Fe=Fl=Fm=Fr=Ga=Gd=Ge=H=He=Hf=Hg=Ho=Hs=I=In=Ir=K=Kr=La=Li=Lr=Lu=Lv= Mc=Md=Mg=Mn=Mo=Mt=N=Na=Nb=Nd=Ne=Nh=Ni=No=Np=O=Og=Os=P=Pa=Pb=Pd=Pm=Po=Pr=Pt=Pu=Ra=Rb=Re=Rf=Rg=Rh=Rn=Ru=S=Sb=Sc=Se=Sg=Si=Sm=Sn=Sr=Ta=Tb=Tc=Te=Th=Ti=Tl=Tm=Ts=U=V=W=Xe=Y=Yb=Zn=Zr= index_label= index2_label= index_comment= index2_comment= CAS_number2= CAS_supplemental2= ATC_prefix2= ATC_suffix2= ATC_supplemental2= PubChem2= PubChemSubstance2= IUPHAR_ligand2= DrugBank2= ChemSpiderID2= UNII2= KEGG2= ChEBI2= ChEMBL2= PDB_ligand2= NIAID_ChemDB2= SMILES2= smiles2= StdInChI2= StdInChIKey2= CAS_number2_Ref= ChEBI2_Ref= ChEMBL2_Ref= ChemSpiderID2_Ref= DrugBank2_Ref= KEGG2_Ref= StdInChI2_Ref= StdInChIKey2_Ref= UNII2_Ref= DTXSID2= QID= QID2=PLLR= pregnancy_US= pregnancy_US_comment= |cat=Pages using infobox drug with unknown parameters |format=0|errNS=0

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| vaccine_type= | mab_type= | _number_of_combo_chemicals={{#invoke:ParameterCount |main |component1 |component2 |component3 |component4|component5|component6 }} | _vaccine_data= | _mab_data= | _mab_vaccine_data= | _mab_other_data=10151NC(Cc1ccccc1)(C)C1S/C10H15N/c1-10(2,11)8-9-6-4-3-5-7-9/h3-7H,8,11H2,1-2H3DHHVAGZRUROJKS-UHFFFAOYSA-NTemplate:StdinchiciteTemplate:Stdinchicite | _combo_data= | _physiological_data= | _clinical_data=Template:Drugs.coma682187Low<ref>Template:Cite book</ref>Physical: Not typical
Psychological: Moderate<ref>Template:Cite book</ref> B3By mouth<ref name=AHFS2019 />Adipex-P, Ionamin, Suprenza, othersPsychostimulant; Appetite suppressant;<ref name=AHFS2019/> Norepinephrine–dopamine releasing agentA08Template:ATC | _legal_data=S4<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>B2Schedule IVRx-only/Anlage IIIClass CSchedule IV

| _other_data=2-methyl-1-phenylpropan-2-amine

| _image_0_or_2 = Fentermina.svg | _image_LR = Phentermine molecule ball.pngPhentermine-3d-CPK.png

| _datapage = Phentermine (data page) | _vaccine_target={{#ifeq: | vaccine | | _type_not_vaccine }} | _legal_all=S4B2Schedule IVSchedule IV | _ATC_prefix_supplemental=A08Template:ATC | _has_EMA_link = | CAS_number=122-09-8 | PubChem=4771 | ChemSpiderID=4607 | ChEBI=8080 | ChEMBL=1574 | DrugBank=DB00191 | KEGG=D05458 | _hasInChI_or_Key={{#if:1S/C10H15N/c1-10(2,11)8-9-6-4-3-5-7-9/h3-7H,8,11H2,1-2H3DHHVAGZRUROJKS-UHFFFAOYSA-N |yes}} | UNII=C045TQL4WP | _hasJmol02 = |_hasMultipleCASnumbers = |_hasMultiplePubChemCIDs = |_hasMultipleChEBIs =

| _countSecondIDs={{#invoke:ParameterCount |main |CAS_number2 |ATC_prefix2 |PubChem2 |PubChemStructure2 |IUPHAR_ligand2 |DrugBank2 |ChemSpiderID2 |UNII2 |KEGG2 |ChEBI2 |ChEMBL2 |PDB_ligand2 |NIAID_ChemDB2 |SMILES2 |smiles2 |StdInChI2 |StdInChIKey2 |DTXCID2}} | _countIndexlabels={{#invoke:ParameterCount |main |index_label |index2_label}} | _trackListSortletter= |QID = |QID2 = |Verifiedfields= |Watchedfields=changed |verifiedrevid=477171245}} Phentermine, sold under the brand name Adipex-P among others, is a medication used together with diet and exercise to treat obesity.<ref name="AHFS2019" /> It is available by itself or as the combination phentermine/topiramate.<ref name="MTM2019">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Phentermine is taken by mouth.<ref name=AHFS2019 />

Common side effects include a fast heart beat, high blood pressure, trouble sleeping, dizziness, and restlessness.<ref name="AHFS2019" /> Serious side effects may include abuse, but do not include pulmonary hypertension or valvular heart disease, as the latter complications were caused by the fenfluramine component of the "fen-phen" combination.<ref name="AHFS2019" /> Phentermine is a norepinephrine and dopamine releasing agent (NDRA) and produces stimulant, rewarding, and appetite suppressant effects.<ref name="RothmanBaumann2003" /><ref name="RothmanBaumann2006" /><ref name="RothmanBaumann2000" /> Chemically, it is a substituted amphetamine.<ref name="Hag2012">Template:Cite journal</ref>

Phentermine was approved for medical use in the United States in 1959.<ref name=AHFS2019>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> It is available as a generic medication.<ref name=AHFS2019/> In 2022, it was the 149th most commonly prescribed medication in the United States, with more than 3Template:Nbspmillion prescriptions.<ref name="Top 300">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Phentermine was withdrawn from the market in the United Kingdom in 2000, while the combination medication fen-phen, of which it was a part, was withdrawn from the market in 1997 due to side effects of fenfluramine.<ref name=Bag2012>Template:Cite book</ref>

Medical uses

Phentermine is used for a short period of time to promote weight loss, if exercise and calorie reduction are not sufficient, and in addition to exercise and calorie reduction.<ref name = TGA/><ref name=USlabel/>

Phentermine is approved for up to 12 weeks of use and most weight loss occurs in the first weeks.<ref name="USlabel" /> However, significant loss continues through the sixth month and has been shown to continue at a slower rate through the ninth month.<ref name=Glazer>Template:Cite journal</ref>

Contraindications

Use is not recommended during pregnancy or breastfeeding,<ref name="Preg2019">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> or with selective serotonin reuptake inhibitors (SSRIs) or monoamine oxidase inhibitors (MAOIs).<ref name="AHFS2019" />

Phentermine is contraindicated for users who:<ref name="TGA" /><ref name="USlabel" />

• have a history of drug abuse
• are allergic to sympathomimetic amine drugs
• are taking a monoamine oxidase inhibitor (MAOI) or have taken one within the last 14 days
• have cardiovascular disease, hyperthyroidism, or glaucoma
• are pregnant, planning to become pregnant, or breastfeeding.

Adverse effects

Tolerance usually occurs; however, risks of dependence and addiction are considered negligible.<ref name=Glazer /><ref name=Haslam >Template:Cite journal</ref> People taking phentermine may be impaired when driving or operating machinery.<ref name=USlabel/> Consumption of alcohol with phentermine may produce adverse effects.<ref name="USlabel" />

There is currently no evidence regarding whether or not phentermine is safe for pregnant women.<ref name="TGA" /><ref name="USlabel" />

Other adverse effects include:<ref name="TGA">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name="USlabel">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

• Cardiovascular effects like palpitations, tachycardia, high blood pressure, precordial pain; rare cases of stroke, angina, myocardial infarction, cardiac failure and cardiac arrest have been reported.
• Central nervous system effects like overstimulation, restlessness, nervousness, insomnia, tremor, dizziness and headache; there are rare reports of euphoria followed by fatigue and depression, and very rarely, psychotic episodes and hallucinations.
• Gastrointestinal effects include nausea, vomiting, dry mouth, cramps, unpleasant taste, diarrhea, and constipation.
• Other adverse effects include trouble urinating, rash, impotence, changes in libido, and facial swelling.

Interactions

Phentermine may decrease the effect of drugs like clonidine, methyldopa, and guanethidine. Drugs to treat hypothyroidism may increase the effect of phentermine.<ref name=USlabel/>

Pharmacology

Pharmacodynamics

Monoamine releasing agent

Template:Nowrap

Compound	Template:Abbrlink	Template:Abbrlink	Template:Abbrlink	Ref
Phenethylamine	10.9	39.5	>10,000	<ref name="ReithBloughHong2015" /><ref name="Forsyth2012">Template:Cite journal</ref><ref name="Blough2008">Template:Cite book</ref>
Dextroamphetamine	6.6–7.2	5.8–24.8	698–1,765	<ref name="RothmanBaumannDersch2001">Template:Cite journal</ref><ref name="BaumannPartillaLehner2013">Template:Cite journal</ref>
Dextromethamphetamine	12.3–13.8	8.5–24.5	736–1,292	<ref name="RothmanBaumannDersch2001" /><ref name="BaumannAyestasPartilla2012">Template:Cite journal</ref>
Phentermine	28.8–39.4	262	2,575–3,511	<ref name="RothmanBaumannDersch2001" /><ref name="Blough2008" /><ref name="PartillaDerschBaumann1999">Template:Cite book</ref>
Chlorphentermine	>10,000 (Template:Abbr)	935–2,650	18.2–30.9	<ref name="RothmanBaumannDersch2001" /><ref name="PartillaDerschBaumann1999" />
Notes: The smaller the value, the more strongly the drug releases the neurotransmitter. The assays were done in rat brain synaptosomes and human potencies may be different. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. Refs: <ref name="RothmanBaumann2003" /><ref name="RothmanBaumann2006" />

Phentermine is a substrate of the monoamine transporters (MATs) and acts as a monoamine releasing agent (MRA), specifically as a norepinephrine–dopamine releasing agent (NDRA).<ref name="RothmanBaumann2003">Template:Cite journal</ref><ref name="RothmanBaumann2006">Template:Cite journal</ref><ref name="RothmanBaumann2000">Template:Cite journal</ref> It also acts as a norepinephrine–dopamine reuptake inhibitor (NDRI) to a lesser extent.<ref name="RothmanBaumann2003" /><ref name="RothmanBaumann2000" /> The drug robustly and dose-dependently elevates brain norepinephrine and dopamine levels in animals.<ref name="RothmanBaumann2003" /> Phentermine is more potent in its effects on norepinephrine than on dopamine and the drug shows only weak effects on serotonin.<ref name="RothmanBaumann2003" /><ref name="RothmanBaumann2006" /><ref name="RothmanBaumann2000" /> Unlike many other amphetamines and MRAs, phentermine is completely inactive at the vesicular monoamine transporter 2 (VMAT2).<ref name="ReithBloughHong2015">Template:Cite journal</ref><ref name="PartillaDempseyNagpal2006">Template:Cite journal</ref> Due to its actions on the catecholamines, phentermine produces effects including stimulation, rewarding effects, appetite suppression, and sympathomimetic effects in animals and humans.<ref name="RothmanBaumann2003" /><ref name="DrugBank" />

In terms of monoamine release in vitro using rat brain synaptosomes, phentermine is about 6-fold less potent than dextroamphetamine in the case of norepinephrine release, 11-fold less potent than dextroamphetamine in the case of dopamine release, and has a ratio of norepinephrine release versus dopamine release of about 6.6:1 compared to dextroamphetamine's ratio of about 3.5:1.<ref name="RothmanBaumann2003" /><ref name="RothmanBaumann2006" /><ref name="RothmanBaumann2000" /> It is more than 3-fold less potent than amphetamine in elevating brain dopamine and serotonin levels in rodents in vivo, is about 10-fold less potent than amphetamine in terms of self-administration in monkeys, and is a relatively weak reinforcer in rodents.<ref name="RothmanBaumann2000" /><ref name="RothmanBloughBaumann2008">Template:Cite book</ref> Although phentermine induces the release of dopamine at sufficiently high concentrations in vitro and at sufficiently high doses in rodents and monkeys in vivo, it may result in only weak or negligible brain dopamine release in humans at typical clinical doses.<ref name="RothmanBaumann2006" /> This may be due to its selectivity for induction of norepinephrine over dopamine release and may be analogous to the case of ephedrine (which is at least 10-fold selective for induction of norepinephrine over dopamine release).<ref name="RothmanBaumann2006" /> The effects of phentermine may be more related to noradrenergic activation rather than dopaminergic activity.<ref name="RothmanBaumann2006" /> However, more research is needed to assess the preceding notions.<ref name="RothmanBaumann2006" />

As with other MRAs, phentermine produces dopaminergic neurotoxicity in rodents at high doses.<ref name="RothmanBaumann2000" /> It can also produce serotonergic neurotoxicity at very high doses in rodents.<ref name="RothmanBaumann2000" /> The clinical significance of these findings for humans, in which employed doses may be much lower, are unclear.<ref name="RothmanBaumann2000" />

The combination of phentermine with a serotonin releasing agent (SRA) like fenfluramine results in suppression of brain dopamine release by phentermine and marked attenuation or abolition of phentermine's stimulant and rewarding effects in animals and humans.<ref name="RothmanBaumann2003" /><ref name="RothmanBaumann2000" /><ref name="RothmanBloughBaumann2008" /><ref name="RothmanBloughBaumann2006">Template:Cite journal</ref><ref name="RothmanBaumann2006b">Template:Cite journal</ref><ref name="RothmanBloughBaumann2007">Template:Cite journal</ref><ref name="BrauerJohanssonSchuster1996">Template:Cite journal</ref> Conversely, combined phentermine and fenfluramine administration synergistically enhances the appetite suppression of these drugs in animals and results in greater weight loss than either drug alone in humans.<ref name="RothmanBaumann2000" /> Fenfluramine produces serotonergic neurotoxicity in animals and addition of phentermine results in either no change or augmentation of this neurotoxicity.<ref name="RothmanBaumann2000" />

Other actions

Phentermine has been found to be completely inactive as a ligand or agonist of the serotonin 5-HT₂ receptors, including of the serotonin 5-HT_2A, 5-HT_2B, and 5-HT_2C receptors.<ref name="RothmanBaumann2006" /><ref name="RothmanBaumann2000" /><ref name="RothmanBloughBaumann2008" /> This is in contrast to the serotonin releasing agents (SRAs) fenfluramine, norfenfluramine, and to a lesser extent chlorphentermine.<ref name="RothmanBaumann2006" /><ref name="RothmanBloughBaumann2008" /> However, another study found that phentermine was a weak human serotonin 5-HT_2C receptor partial agonist (Template:Abbrlink = 1,394Template:NbspnM, V_max = 66%).<ref name="RothmanBloughBaumann2008" /> In accordance with its lack of serotonin release and serotonin 5-HT_2B receptor agonism, phentermine appears to show no risk of primary pulmonary hypertension (PPH) or valvular heart disease (VHD) in humans.<ref name="RothmanBaumann2002">Template:Cite journal</ref><ref name="RothmanBaumann2000" /><ref name="RothmanBloughBaumann2008" />

Phentermine has been found to be active as an agonist of the rat and human trace amine-associated receptor 1 (TAAR1).<ref name="BarakSalahpourZhang2008">Template:Cite journal</ref><ref name="LewinNavarroMascarella2008">Template:Cite journal</ref><ref name="KimShinBae2021">Template:Cite journal</ref><ref name="BunzowSondersArttamangkul2001">Template:Cite journal</ref> It appears to be a weak human TAAR1 partial agonist (Template:Abbr = 5,470Template:NbspnM and Template:Abbrlink = 68% in one study).<ref name="LewinNavarroMascarella2008" /> The drug shows reduced activity as a TAAR1 agonist compared to amphetamine.<ref name="LewinNavarroMascarella2008" /><ref name="BunzowSondersArttamangkul2001" /> TAAR1 agonism by amphetamines that possess this action may serve to auto-inhibit and constrain their effects.<ref name="EspinozaGainetdinov2014">Template:Cite book</ref><ref name="KuropkaZawadzkiSzpot2023">Template:Cite journal</ref><ref name="SimmlerBuserDonzelli2013">Template:Cite journal</ref><ref name="DiCaraMaggioAloisi2011">Template:Cite journal</ref>

Phentermine is a very weak monoamine oxidase inhibitor (MAOI) in vitro.<ref name="Reyes-ParadaIturriaga-VasquezCassels2019">Template:Cite journal</ref><ref name="RothmanBaumann2000" /><ref name="UlusMaherWurtman2000">Template:Cite journal</ref> It specifically inhibits monoamine oxidase A (MAO-A) (Template:Abbrlink = 85,000–143,000Template:NbspnM) and monoamine oxidase B (MAO-B) (Template:Abbr = 285,000Template:NbspnM).<ref name="Reyes-ParadaIturriaga-VasquezCassels2019" /><ref name="RothmanBaumann2000" /><ref name="UlusMaherWurtman2000" /> However, its potency as a MAOI is far below its potency as a monoamine releasing agent.<ref name="RothmanBaumann2000" /> Relatedly, phentermine does not show neurochemical signs of MAOI activity in rodents in vivo.<ref name="RothmanBaumann2000" /> As such, the significance of phentermine as an MAOI in humans is questionable.<ref name="RothmanBaumann2000" />

Pharmacokinetics

Absorption

The pharmacokinetics of phentermine are dose-dependent.<ref name="DrugBank">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Peak concentrations of phentermine are reached 6Template:Nbsphours following oral administration of a dose of 15Template:Nbspmg.<ref name="DrugBank" /> The steady-state levels of phentermine with continuous administration have been found to be around 200Template:Nbspng/mL in clinical studies.<ref name="DrugBank" /> The oral bioavailability of phentermine is not affected by intake of a high-fat meal.<ref name="DrugBank" />

Distribution

The volume of distribution of phentermine is 5Template:NbspL/kg.<ref name="DrugBank" /> Its plasma protein binding is approximately 17.5%.<ref name="DrugBank" />

Metabolism

Phentermine undergoes minimal metabolism.<ref name="DrugBank" /> Only about 6% of an administered dose of phentermine is metabolized.<ref name="DrugBank" /> It is metabolized to a minor extent by para-hydroxylation, N-oxidation, and N-hydroxylation, followed by conjugation.<ref name="DrugBank" />

Elimination

The drug is eliminated mainly in urine.<ref name="DrugBank" /> It is excreted 62 to 85% unchanged in urine.<ref name="DrugBank" /> The elimination half-life of phentermine is 20 to 25Template:Nbsphours.<ref name="DrugBank" /><ref name="TGA" /> The elimination of phentermine is modified by urine acidicity or pH.<ref name="DrugBank" /><ref name="TGA" /> In the case of acidic urine (pH < 5), the elimination half-life of phentermine has been found to be 7 to 8Template:Nbsphours.<ref name="DrugBank" /> The clearance of phentermine is 8.79Template:NbspL/h.<ref name="DrugBank" />

History

File:Phentermine.jpg

In 1959, phentermine first received approval from the US Food and Drug Administration (FDA) as an appetite suppressant.<ref name="Ryan">Template:Cite book</ref> Eventually a hydrochloride salt and a resin form became available.<ref name="Ryan" />

Phentermine was marketed with fenfluramine or dexfenfluramine as a combination appetite suppressant and fat burning agent under the popular name fen-phen.<ref>Template:Cite news</ref> In 1997, after 24 cases of heart valve disease in fen-phen users, fenfluramine and dexfenfluramine were voluntarily taken off the market at the request of the FDA.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Studies later showed nearly 30% of people taking fenfluramine or dexfenfluramine for up to 24 months had abnormal valve findings.<ref name=2003rev>Template:Cite journal</ref>

Phentermine is still available by itself in most countries, including the US.<ref name=Ryan/> However, because it is similar to amphetamine, it is classified as a controlled substance in many countries. Internationally, phentermine is a schedule IV drug under the Convention on Psychotropic Substances.<ref>Convention on Psychotropic Substances Template:Webarchive</ref> In the United States, it is classified as a Schedule IV controlled substance under the Controlled Substances Act. In contrast, amphetamine preparations are classified as Schedule II controlled substances.<ref>Template:Cite journal</ref>

A company called Vivus developed a combination drug, phentermine/topiramate that it originally called Qnexa and then called Qsymia, which was invented and used off-label by Thomas Najarian, who opened a weight-clinic in Los Osos, California in 2001; Najarian had previously worked at Interneuron Pharmaceuticals, which had developed one of the fen-phen drugs previously withdrawn from the market.<ref name=NYT2012>Template:Cite news</ref> The FDA rejected the combination drug in 2010 due to concerns over its safety.<ref name=NYT2012/> In 2012 the FDA approved it after Vivus re-applied with further safety data.<ref>Template:Cite news</ref> At the time, one obesity specialist estimated that around 70% of his colleagues were already prescribing the combination off-label.<ref name=NYT2012/>

Chemistry

Phentermine, also known as α,α-dimethylphenethylamine or as α-methylamphetamine, is a substituted phenethylamine and amphetamine.<ref name="PubChem">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name="Elks2014">Template:Cite book</ref><ref name="IndexNominum2000">Template:Cite book</ref> It is the derivative of amphetamine in which a second methyl group is present at the alpha carbon.<ref name=Hag2012 /><ref name="PubChem" /><ref name="Elks2014" /><ref name="IndexNominum2000" /> The drug is a positional isomer of methamphetamine (N-methylamphetamine) and of other methylamphetamines such as 4-methylamphetamine.<ref name="PubChem" /><ref name="Elks2014" /><ref name="IndexNominum2000" />

Derivatives

A number of derivatives of phentermine exist, including cericlamine, chlorphentermine, cloforex, clortermine, etolorex, mephentermine, 3,4-methylenedioxyphentermine (MDPH), 3,4-methylenedioxy-N-methylphentermine (MDMP or MDMPH), and pentorex, among others.<ref name="Elks2014" /><ref name="IndexNominum2000" /> Some of these drugs, including chlorphentermine, cloforex, clortermine, and mephentermine, have been marketed as pharmaceutical drugs similarly to phentermine, for instance as appetite suppressants.<ref name="Elks2014" /><ref name="IndexNominum2000" />

Society and culture

Etymology

The term ‘phentermine' is contracted from phenyl-tertiary-butyl amine.

Brand names

Phentermine is marketed under many brand names and formulations worldwide, including Acxion, Adipex, Adipex-P, Duromine, Elvenir, Fastin, Ionamin, Lomaira (phentermine hydrochloride), Panbesy, Qsymia (phentermine and topiramate), Razin, Redusa, Sentis, Suprenza, and Terfamex.<ref name=drugs.com>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

External links

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