Download - Amini dopolnjeno
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AMINI inALKALOIDI
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HN3
Ka = 1,2 ⋅10-5
HCNKa = 2,1⋅10-9
N2H4
Kb = 8,5 ⋅10-7
NH3
Kb = 1,8 ⋅10-5
HNO3
Ka = 20
HNO2
Ka=6 ⋅10-4
Organske nitro spojine
Nitrozo spojine
Alkil azidi
Cianidi (nitrili)
Alkil hidrazini
Alkil amini
Anorganske dušikove spojine in njihovi organski analogi
R N O
R N+ O
O
R C N
R N N H
HH
R N H
H
R N3
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Primarni, sekundarni in terciarni amini
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Topnost aminov v vodi
Topnost v vodi: 482 g/L pri 25 oC
Topnost v vodi: 0,061 g/L pri 20 oC 1000 g/L pri 25 oC
Topnost v vodi: 1,8 g/L pri 25 oC 34 g/L pri 25 oC
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butilamin
acetilklorid
δ −
δ −
δ +
Nu-
Amini kot nukleofili – nukleofilna adicija na karbonilno skupino
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Amini kot nukleofili
ClC
O
N
H
H
C
O
Cl
N+
H
H
C
O
N
H
+ HCl
amidna oz. peptidna vez
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N
H
N
H
N
Hetrociklični amini
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Pikasti mišjak
l. 399 BCSokrat
Alkaloidi v zgodovini - že v antikiAlkaloidi v zgodovini - že v antikiza zastrupljanjeza zastrupljanje
Derivat piperidina
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Kleopatra 69-30 BCAtropa belladonna
Egipt - za ličenje Egipt - za ličenje
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Južna Amerika kot orožje – Južna Amerika kot orožje – strup za puščice (kurare)strup za puščice (kurare)
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Lewis Carroll - Alice in Wonderland Thomas De Quincey (1785-1859) in 1820 wrote "Confessions of an English Opium Eater." Edgar Allen Poe wrote (1809-1849) - "Pit & the Pendulum". Samuel T. Coleride (1772-1836) wrote the poem "Kubla Khan."Elizabeth Barrett Browning (1806-18610 - British poet.
Literarna dela pod vplivom opiatovLiterarna dela pod vplivom opiatov
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O
OH
OH
N
O
OAc
N
AcO
O
ACO
OH
Nmorfin heroin
kodein
CH3 C
O
Cl2
CH3 C
O
Cl
l. 1806
OPIATIOPIATI
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Testi za heroinTesti za heroin
• OPI test – osnova je OPI test – osnova je imunoesej (alergen - imunoesej (alergen - protitelo)protitelo)
• Morfin se izloči v urin v Morfin se izloči v urin v obliki morfin-3-obliki morfin-3-glukuronida v manjši meri glukuronida v manjši meri pa v obliki prostega pa v obliki prostega morfina in drugih morfina in drugih metabolitov.metabolitov.
• IgG - imunoglobulin G IgG - imunoglobulin G najbolj pogosto protitelo najbolj pogosto protitelo in mišja monoklonska in mišja monoklonska antitelesca za opiate.antitelesca za opiate.
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Rutinski testiRutinski testi
Hitri barvni testi za heroin, morfin in druge opiate so osnovani na: •reakciji vzorca z Marquis-jevim reagentom(HCO v žveplovi kislini) ali Mecke-jevim reagentom (selenova kislina v koncentrirani žveplovi kislini) in vrednotenja intenzitete barve•reakciji z HNO2 kislino za razlikovanje med heroinom in morfinom.
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Učinki opiatovUčinki opiatov
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ALKALOIDI V STRUPENIH IZLOČKIHALKALOIDI V STRUPENIH IZLOČKIHŽIVALI - REDKIŽIVALI - REDKI
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Strupi pajkovStrupi pajkov: Araneidae Araneidae družinadružina
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AcAciilpollpoliiaminaminski neurotoksiniski neurotoksini
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TROPANSKI ALKALOIDITROPANSKI ALKALOIDI
Tropanski obročTropanski obroč DaturaDatura
Motijo akcijo neurotransmitorjaMotijo akcijo neurotransmitorjaacetilholina, kar je osnova za acetilholina, kar je osnova za anestetične lastnosti.anestetične lastnosti.
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Plantažekoke in sušenje
KokainKokain
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Skeletna formula kokaina - tropan alkaloid
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Pirolidinski alkaloidi (tropanski) – L-ornitina glutamata
Piperidinski - L-lizina Piridinski - L-fenilalanina
Kinolinski – L-triptofana
Alkaloidi - metaboliti aminokislinAlkaloidi - metaboliti aminokislin
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Izokinolinski – L- tirozina Indol – L-triptofana
Purinski alkaloidi – aspartata, glicina in glutamina
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“Ogenj Sv. Antona”- ergotizem
Pieter Bruegel (1525 – 1569)
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Lizergova kislina LSD
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Naravni LSDNaravni LSD
Jutranja slava Jutranja slava Ipomoea tricolor
V semenih se nahaja alkaloidV semenih se nahaja alkaloidergin – naravni LSDergin – naravni LSD
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Kaktusi: Kaktusi: Psilocybe, Paneolus, Psilocybe, Paneolus, ConocybeConocybe
Indolni obroč – motijo ali tekmujejo z delovanjme možganskega transmitorja serotonina.
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ViriViri
• http://www.friedli.com/herbs/phytochem/alkaloids/alkaloid1.html
• http://www.herbs2000.com/h_menu/alkaloids.htm
• http://www.biologie.uni-hamburg.de/b-online/e20/20a.htm
• http://goldbook.iupac.org/A00220.html