Nialamide

There is also a fermentation route to netilmicin as noted by Kleeman Engel. 

Chemical Name 4-Pyridinecarboxyllc acid 2-[3-oxo-3-[(phenylmethyl)-amino] propyl] hy-drazide 

Trade Name Manufacturer Country Year Introduced 

Methyl acrylate, 28.0 g (0.4 mol) was added dropwise during one hour to a solution containing 543 g (0.4 mol) of isonicotinic acid hydrazide (isoniazid) and 10 ml of glacial acetic acid in 400 ml of tertiary butyl alcohol. The resulting solution then was heated for 18 hours on a steam bath. Concentration of the reaction mixture to 100 ml yielded 13.0 g of unreacted isonicotinic acid hydrazide. The filtrate was concentrated to a thick syrup which was triturated 

A slurry of 75 g (0.034 mol) of 1-i8onicotinvl-2-(carbomethoxvethyl)-hvdrazine and 5 ml of benzylamine is heated with stirring at 130 C for three hours. The cooled mass is then recrystallized from ethyl acetate to yield white needles melting at 151.1°C to 152.1 C. 

---

Nialamide [51 -12-7] (30) and mebana2ine [65-64-5] (31) are two MAO inhibitors marketed in Europe that have stmctural similarities to ipronia2id and pheneUine, respectively. Both compounds are prepared by standard methods (35,36). 

Thus, condensation of isoniazide with acetone at the basic nitrogen gives the corresponding Shiff base (8). Catalytic reduction affords the antidepressant, iproniazid (9). Addition of the same basic nitrogen to methyl acrylate by Michael condensation leads to the 3-amino ester (10). This is converted to the amide, nialamide (11), on heating with benzylamine. 

Carbenicillin disodlum N-Benzylamine Antazoline HCI Beclamide Nialamide Reproterol 2-Benzylaniline Mianserin N-6enzylaniline Bepridil... 

C4H(j02 96-33-3) see Aminoglutethimide Eprosartan Glutethimide Hexobendine Levocabastine Nialamide Phenglutarimide Pioglitazone Remifentanil Vincamine acrylonitrile... 

C7H()N 100-46-9) see Amosulalol Bamidipine Beclamide Benperidol Betanidine Biotin Cisapride Dilevalol Guanoxan Moxifloxacin hydrochloride NebivOlol Nialamide Reproterol Sparfloxacin Sulbentine Viloxazine benzylamine hydrochloride (C7H,()C1N 3287-99-8) see Benzyl mustard oil 2-benzylaminoethanol... 

C(,H7NjO 54-85-3) see Glyconiazide Iproniazid Nialamide Pasiniazid Streptoniazid isonicotinamidc... 

QjHf NjO 1453-82-3) see Cefsulodin Lsonicotinic acid 2-(2-carboxyethyl)hydrazide methyl ester (C111H17N3O7 90872-10-9) see Nialamide isonicotinoyl chloride... 

Further evidence for serotonergic mediation of the effects of hallucinogens was provided by a report on the development of functional supersensitivity in the rat with a chronic denervation of spinal 5-HT neurons. Nygren et al. (138) reported that rats pretreated with intracistemally administered 5,6-dihydroxy-tryptamine (5,6-DHT), a 5-HT neurotoxin, subsequently showed greater hindlimb extensor facilitations to 5-MeODMT or L-tryptophan + nialamide at 1 week versus 1 day following pretreatment. 

We recently extended this line of research to include cat behavior (J. Heym and B. L. Jacobs, unpublished observations). Cats were given a daily injection of nialamide (5 mg/kg i.p.) for 1 week and then tested with LSD, DOM, or apomorphine at various times after the drug was withdrawn. The behavioral... 

With most psychedelics, their activity can probably be considerably enhanced by prior (or possibly concomitant) use of a monoamine oxidase inhibitor (e.g., isocarboxazid (Marplan), nialamide (Niamid), phenelzine (Nardil), and tranylcypromine (Parnate)). Some compounds (e.g., DMT) which have no oral activity, can probably become orally active. These compounds are often prescribed as antidepressants, but it is not a good idea to use them frequently or in large doses. For antidotes to the hallucinogens see Amer. J. Hosp. Pharm. 30,80(1973). 

Increased bilirubin levels are caused due to the intake of large doses of such drugs as chloroquine, vitamin K, sulpha-drugs, tetracyclines, paracetamol, nicotinic acid and monoamine oxidase inhibitors (e.g., iproniazid RP 1.0 nialamide RP 1.8 isocarboxazid RP 3.1 phenelzine RP 18 pheniprazine RP31 and tranylcypromine RP 45), where RP designates the Relative Potency based on the tiyptamine potentiation test. The elevated levels are due to hepatic injury, and... 

Neurotransmitters, in regulation of blood pressure, 55 Nialamide, 254 Nicotinic acid, 253 Nicotinyl alcohol, 253 Nidroxyzone, 228 Nifenazone, 234 Niflvminic acid, 256 Nifurprazine, 231 Nikethamide, 253 Nitrazepam, 366 Nitrimidazine, 240 Nitrofurantoin, 230 Nitrofuratel, 229 Nitrofurazone, 228 5-Nitrofurfural, 228 Nitrofuroxime, 228 Nitrosation... 

Iproniazic was the first widely prescribed MAOI. Realization that this drug can produce rare but dangerous liver toxicity led to the synthesis of the other hydrazine MAOIs, such as isocarboxazid, nialamide, and phenelzine, as well as the nonhydrazine MAOIs, tranylcypromine, and pargyline. 

During clinical studies of iproniazid (201) in the treatment of tuberculosis it was found to have a mood-elevating effect. It was later found to be an inhibitor of monoamine oxidase (MAO), the enzyme which oxidatively deaminates such neurotransmitters as noradrenaline and serotonin, and it was tried in the treatment of depression in 1957. Other MAO inhibitors were introduced later, most of them being hydrazine derivatives. Heterocyclic examples include isocarboxazid (202) and nialamide (203). They are toxic and cause dangerous hypertensive crises if food with a high tyramine content is eaten, and on this account their use is limited. 

Nialamide [51-12-1] - piTAMINS - NIACINE,NICOTINAMIDEAND NICOTINIC ACID] pol25) - pYRIDINEAND PYRIDINEDERIVATIVES] po120)... 

---