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Alkaloids by Mind Map: Alkaloids

1. L-Ornithine

1.1. Pyrrolidine and Tropane alkaloids

1.1.1. Biosynthesis

1.1.1.1. Pyrrolidine alkaloids from N-methyl-delta1-pyrrolinium cation and acetylCoA

1.1.1.2. Tropane alkaloids

1.1.2. Examples

1.1.2.1. Cocaine

1.1.2.1.1. Sources

1.1.2.1.2. Activities

1.1.2.1.3. Coca leaves

1.1.2.2. Atropine and Hyoscyamine

1.1.2.2.1. Chemistry

1.1.2.2.2. Scopolamine (Hyoscine)

1.1.2.2.3. Activities

1.1.2.2.4. Sources

1.2. Pyrrolizidine alkaloids

1.2.1. Asteraceae and Boraginaceae

1.2.2. Hepatotoxic

1.2.2.1. Double bond at 1,2 in ring and ester

1.2.2.2. liver oxidase in mammals => alkylating agent

2. L-Lysine

2.1. Examples

2.1.1. Piperidine alkaloids

2.1.1.1. Pelletierine

2.1.1.1.1. Punica granatum

2.1.1.1.2. antihelminth in dogs

2.1.1.2. Lobeline

2.1.1.2.1. Lobeline chinensis (พระจันทร์ครึ่งซัก)

2.1.1.2.2. Campanulaceae

2.1.1.2.3. bronchodilator and expectorant

2.1.1.3. Piperine'

2.1.1.3.1. Piper longum (ดีปลี)

2.1.1.3.2. Piper niger (พริกไทย)

2.1.1.4. quinolizidine alkaloids

2.1.1.4.1. Leguminosae (Fabaceae)

2.1.1.4.2. Toxic

2.1.1.5. Indolizidine akjakiuds

2.1.1.5.1. fused six membered ring and five member ring with N at the center

2.1.1.5.2. Swainsonine

2.1.1.5.3. Castanospermine

3. Phenylanine and Tyrosine

3.1. Phenethylamines

3.1.1. Protoalkaloids

3.1.2. From Tyrosine

3.1.2.1. Mescaline

3.1.2.1.1. Peyote (Lophophora fam. Cactaceae)

3.1.2.1.2. Catecholamines

3.1.2.1.3. Euphoria

3.1.2.1.4. Hallucinogenic

3.1.3. From Phenylalanine

3.1.3.1. Ephredine and Pseudoephredine

3.1.3.1.1. sources

3.1.3.1.2. Activity

3.1.3.1.3. Pseudoephredine is an diastereomer of ephredine

3.1.3.2. (-)-Cathinone

3.1.3.2.1. sources

3.1.3.2.2. MOAI

3.2. Isoquinoline alkaloids

3.2.1. Simple tetrahydroisoquinoline alkaloids

3.2.1.1. Phenylethylamine + pyruvic acid or glyoxylic acid

3.2.1.2. Cactaceae

3.2.1.3. Chenopodiaceae

3.2.1.4. Fabaceae

3.2.2. Benzyltetrahydroisoquinoline alkaloids

3.2.2.1. From Tyrosine

3.2.2.1.1. Dopamin + 4-hydroxyphenyl acetaldehyde

3.2.2.2. 5 Class

3.2.2.2.1. Simple Benzylioquinoline

3.2.2.2.2. Bisbenzyltetrahydroisoquinolines

3.2.2.2.3. Aporphinoids

3.2.2.2.4. Protoberberines

3.2.2.2.5. Morphinan alkaloids

3.2.3. Phenylethylisoquinoline alkaloids

3.2.3.1. 7 membered ring analog of apophinoids

3.2.3.2. Colchicine

3.2.3.2.1. Autumn crocus (Liliaceae)

3.2.3.2.2. Gloriosa superba (Lilibaceae) ดองดึง

3.2.3.2.3. antigout

3.2.3.2.4. polyploidy of chromosome

3.2.4. Monoterpenoid tetrahydroisoquinoline alkaloids

3.2.4.1. dopamine + secologanin

3.2.4.2. Emetine

3.2.4.2.1. Ipecacuanha (Rubiaceae)

3.2.4.2.2. Amoebic dysentery

3.2.4.2.3. Emetic

3.2.5. Amaryllidaceae alkaloids

3.2.5.1. Gallantamine

3.2.5.1.1. Antialzhiemer

4. Tryptophan

4.1. Indole

4.1.1. Simple indole alkaloids

4.1.1.1. Small subtituted tryptamin

4.1.1.2. Serotonin

4.1.1.3. Psylocybin , Psylocin

4.1.1.3.1. Same as LSD

4.1.1.3.2. Psylocybin is prodrug of pstlodin

4.1.1.3.3. 1000 times less activity than LSD

4.1.1.3.4. Narcotic

4.1.1.3.5. Serotonin distubance

4.1.1.3.6. เห็ดขี้ควาย เสพติดประเภท 5

4.1.2. Simple beta-carboline alkaloids

4.1.2.1. Fused 3 rings => benzen indole pyridine

4.1.2.2. Manich-like reaction

4.1.2.3. Harmine, Harman, Harmaline

4.1.2.3.1. MOAI

4.1.2.3.2. Serotonin receptor agonist

4.1.2.3.3. Halucinogen

4.1.2.3.4. sources

4.1.3. Terpenoid indole alkaloids

4.1.3.1. Strychnine

4.1.3.1.1. High toxicity

4.1.3.1.2. CNS active (glycine receptor)

4.1.3.1.3. Spasm, Fatal Seizure

4.1.3.1.4. เจริญอาหาร

4.1.3.1.5. เบื่อหนุ

4.1.3.1.6. ห้ามใช้เป็นยาแผนโบราณ ยกเว้นที่ dose < 60 mg

4.1.3.1.7. sources

4.1.3.2. C-Toxiferine

4.1.3.2.1. Bis-iondole alkaloids

4.1.3.2.2. Curare

4.1.3.3. Yohimbine

4.1.3.3.1. Yohimbe (Rubiaceae)

4.1.3.3.2. Alpha 2 adrenergic antagonist

4.1.3.4. Ellipticine

4.1.3.4.1. Apocynaceae

4.2. quinoline