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First generation antihistamine
Mepyramine , also known as pyrilamine , is a first generation antihistamine , targeting the H1 receptor as an inverse agonist .[1] Mepyramine rapidly permeates the brain, often causing drowsiness .[2] It is often sold as a maleate salt, pyrilamine maleate .
The medication has negligible anticholinergic activity, with 130,000-fold selectivity for the histamine H1 receptor over the muscarinic acetylcholine receptors (for comparison, diphenhydramine had 20-fold selectivity for the H1 receptor).[3]
It was patented in 1943 and came into medical use in 1949.[4] It was marketed under the names Histadyl, Histalon, Neo-Antergan, Neo-Pyramine, and Nisaval.[5] In the 1960s and 70s it was a very common component in over-the-counter sleep aids such as Alva-Tranquil, Dormin, Sedacaps, Sominex , Nytol, and many others.[5] The US FDA included it in the list of chemicals and compounds barred from use in over-the-counter nighttime sleep aid products in 1989.[6]
It is used in over-the-counter combination products to treat the common cold and menstrual symptoms such as Midol Complete .[7] It is also the active ingredient of the topical antihistamine creams Anthisan[8] and Neoantergan[1] sold for the treatment of insect bites, stings, and nettle rash.
See also References
Psychedelics (5-HT2A agonists)
Benzofurans Lyserg‐ amides Phenethyl‐ amines
2C-x 25x -NBx
25x -NB 25x -NB3OMe 25B-NB3OMe 25C-NB3OMe 25D-NB3OMe 25E-NB3OMe 25H-NB3OMe 25I-NB3OMe 25N-NB3OMe 25P-NB3OMe 25T2-NB3OMe 25T4-NB3OMe 25T7-NB3OMe 25TFM-NB3OMe 25x -NB4OMe 25B-NB4OMe 25C-NB4OMe 25D-NB4OMe 25E-NB4OMe 25H-NB4OMe 25I-NB4OMe 25N-NB4OMe 25P-NB4OMe 25T2-NB4OMe 25T4-NB4OMe 25T7-NB4OMe 25TFM-NB4OMe 25x -NBF 25x -NBMD 25B-NBMD 25C-NBMD 25D-NBMD 25E-NBMD 25F-NBMD 25H-NBMD 25I-NBMD 25P-NBMD 25T2-NBMD 25T7-NBMD 25TFM-NBMD 25x -NBOH 25x -NBOMe Atypical structures
25x -NMx 25B-NMe7BF 25B-NMe7BT 25B-NMe7Bim 25B-NMe7Box 25B-NMe7DHBF 25B-NMe7Ind 25B-NMe7Indz 25B-NMePyr 25I-NMe7DHBF 25I-NMeFur 25I-NMeTHF 25I-NMeTh N-(2C)-fentanyl N-(2C-B) fentanyl N-(2C-C) fentanyl N-(2C-D) fentanyl N-(2C-E) fentanyl N-(2C-G) fentanyl N-(2C-H) fentanyl N-(2C-I) fentanyl N-(2C-IP) fentanyl N-(2C-N) fentanyl N-(2C-P) fentanyl N-(2C-T) fentanyl N-(2C-T-2) fentanyl N-(2C-T-4) fentanyl N-(2C-T-7) fentanyl N-(2C-TFM) fentanyl
3C-x 4C-x DOx HOT-x MDxx Mescaline (subst.) TMAs TMA TMA-2 TMA-3 TMA-4 TMA-5 TMA-6 Others
Piperazines Tryptamines
alpha -alkyltryptaminesx -DALT x -DET x -DiPT x -DMT 4,5-DHP-DMT 2,N,N-TMT 4-AcO-DMT 4-HO-5-MeO-DMT 4,N,N-TMT 4-Propionyloxy-DMT 5,6-diBr-DMT 5-AcO-DMT 5-Bromo-DMT 5-MeO-2,N ,N -TMT 5-MeO-4,N ,N -TMT 5-MeO-α,N,N-TMT 5-MeO-DMT 5-N ,N -TMT 7,N,N-TMT α,N,N-TMT (Bufotenin) 5-HO-DMT DMT Norbaeocystin (Psilocin) 4-HO-DMT (Psilocybin) 4-PO-DMT x -DPT Ibogaine-related x -MET x -MiPT Others
Others
Dissociatives (NMDAR antagonists )
Deliriants (mAChR antagonists ) Others
H1
Agonists Antagonists Others: Atypical antipsychotics (e.g., aripiprazole , asenapine , brexpiprazole , brilaroxazine , clozapine , iloperidone , olanzapine , paliperidone , quetiapine , risperidone , ziprasidone , zotepine )Phenylpiperazine antidepressants (e.g., hydroxynefazodone , nefazodone , trazodone , triazoledione )Tetracyclic antidepressants (e.g., amoxapine , loxapine , maprotiline , mianserin , mirtazapine , oxaprotiline )Tricyclic antidepressants (e.g., amitriptyline , butriptyline , clomipramine , desipramine , dosulepin (dothiepin) , doxepin , imipramine , iprindole , lofepramine , nortriptyline , protriptyline , trimipramine )Typical antipsychotics (e.g., chlorpromazine , flupenthixol , fluphenazine , loxapine , perphenazine , prochlorperazine , thioridazine , thiothixene )Unknown/unsorted: AzanatorBelarizine Elbanizine Flotrenizine GSK1004723 Napactadine Tagorizine Trelnarizine Trenizine
H2
H3
H4
DAT Tooltip Dopamine transporter (DRIs Tooltip Dopamine reuptake inhibitors )
NET Tooltip Norepinephrine transporter (NRIs Tooltip Norepinephrine reuptake inhibitors )
Others: Antihistamines (e.g., brompheniramine , chlorphenamine , pheniramine , tripelennamine )Antipsychotics (e.g., loxapine , ziprasidone )Arylcyclohexylamines (e.g., ketamine , phencyclidine )Dopexamine Ephenidine Ginkgo biloba Indeloxazine Nefazodone Opioids (e.g., desmetramadol , methadone , pethidine (meperidine) , tapentadol , tramadol , levorphanol )
SERT Tooltip Serotonin transporter (SRIs Tooltip Serotonin reuptake inhibitors )
Others: A-80426Amoxapine Antihistamines (e.g., brompheniramine , chlorphenamine , dimenhydrinate , diphenhydramine , mepyramine (pyrilamine) , pheniramine , tripelennamine )Antipsychotics (e.g., loxapine , ziprasidone )Arylcyclohexylamines (e.g., 3-MeO-PCP , esketamine , ketamine , methoxetamine , phencyclidine )Cyclobenzaprine Delucemine Dextromethorphan Dextrorphan Efavirenz Hypidone Medifoxamine Mesembrine Mifepristone MIN-117 (WF-516) N-Me-5-HT Opioids (e.g., dextropropoxyphene , methadone , pethidine (meperidine) , levorphanol , tapentadol , tramadol )Roxindole
VMATs Tooltip Vesicular monoamine transporters Others